[ CAS No. 1003-61-8 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 1003-61-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1003-61-8 ]

SDS Specification

Alternatived Products of [ 1003-61-8 ]

Product Details of [ 1003-61-8 ]

CAS No. :	1003-61-8	MDL No. :	MFCD02179570
Formula :	C₄H₄N₂OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HZKMBJCDAXLMDN-UHFFFAOYSA-N
M.W :	128.15	Pubchem ID :	2737798
Synonyms :

Calculated chemistry of [ 1003-61-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	31.91
TPSA :	84.22 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.8 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.82
Log Po/w (XLOGP3) :	0.4
Log Po/w (WLOGP) :	0.55
Log Po/w (MLOGP) :	-1.17
Log Po/w (SILICOS-IT) :	1.6
Consensus Log Po/w :	0.44

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.28
Solubility :	6.68 mg/ml ; 0.0521 mol/l
Class :	Very soluble
Log S (Ali) :	-1.73
Solubility :	2.36 mg/ml ; 0.0184 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.84
Solubility :	18.4 mg/ml ; 0.143 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.06

Safety of [ 1003-61-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H317-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1003-61-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1003-61-8 ]
Downstream synthetic route of [ 1003-61-8 ]

[ 1003-61-8 ] Synthesis Path-Upstream 1~1

1
[ 1003-61-8 ]
[ 131184-73-1 ]

Yield	Reaction Conditions	Operation in experiment
43%	With sodium tetrahydroborate In methanol for 1 h; Cooling with ice	2-Amino-5-formylthiazole (11.5 g, 90 mmol) was dissolved in methanol (120 mL), and sodium borohydride (5.11 g, 135 mmol) was added thereto while cooling with ice, followed by stirring at the same temperature for 1 hour. Acetone (6 mL) and water (10 mL) were added to the reaction mixture, followed by stirring. The residue obtained by evaporating the reaction mixture under reduced pressure was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:15), thereby giving the title compound (5.09 g, 43percent) as a white solid.

Reference： [1] Farmaco, 1989, vol. 44, # 11, p. 1011 - 1030
[2] Patent: US2013/165438, 2013, A1, . Location in patent: Paragraph 0349

[ 1003-61-8 ] Synthesis Path-Downstream 1~12

1
[ 1003-61-8 ]
[ 108-24-7 ]
[ 252662-37-6 ]

Reference： [1]Journal of Medicinal Chemistry,1969,vol. 12,p. 374 - 379

2
[ 1003-61-8 ]
[ 105-53-3 ]
[ 305330-37-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 1151 - 1175

3
[ 1003-61-8 ]
[ 38870-89-2 ]
N-(5-formylthiazol-2-yl)-2-methoxyacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 2.5h;	Example 1-15 Synthesis of the present aldehyde derivative [Compound No. (w)] To a solution of 2.50 g of <strong>[1003-61-8]2-amino-5-formylthiazole</strong> and 2.44 g of triethylamine in 30 ml of tetrahydrofuran was added dropwise a solution of 2.22 g of methoxyacetyl chloride in 8 ml of tetrahydrofuran under ice-cooling, and the mixture was stirred at room temperature for 2 hours and 30 minutes. Insolubles were filtered, and the filtrate was added to ice water and then extracted with ethyl acetate. An organic layer was washed with 10% hydrochloric acid and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 2.83 g of N-(5-formylthiazol-2-yl)-2-methoxyacetamide [Compound No. (w)] as pale yellow powder. 1H-NMR (270MHz, DMSO-d6) delta (ppm): 3.36 (s, 3H), 4.22 (s, 2H), 8.42 (s, 1H), 9.97 (s, 1H).

Reference： [1]Patent: EP1857455,2007,A1 .Location in patent: Page/Page column 101

4
[ 1003-61-8 ]
C₁₅H₁₉ClO₃S [ No CAS ]
[ 1001419-48-2 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; at 20℃; for 16h;Product distribution / selectivity;	Oxalyl chloride (203 muL of a 2 M solution in DCM; 0.406 mmol) was added to a 0 C. mixture of Example 1 Part D compound (80 mg; 0.270 mmol) in DCM (0.70 mL). DMF (10 uL) was added. Gas evolution occurred. The reaction mixture was stirred at RT for 1.5 h, then was concentrated in vacuo. The residue was stripped from CHCl3 (2×2 mL). The crude acid chloride was dissolved in DCM (0.90 mL). <strong>[1003-61-8]2-amino-5-formylthiazole</strong> (45.0 mg; 0.351 mmol) was added followed by pyridine (66.0 uL; 0.810 mmol). After 16 h at RT the reaction was concentrated in vacuo. The crude product was chromatographed (SiO2; continuous gradient from 0 to 100% solvent B over 6 min, hold at 100% solvent B for 8 min, where solvent A=hexanes and solvent B=EtOAc) to give Part A compound (27 mg; 25%).

Reference： [1]Patent: US2008/9465,2008,A1 .Location in patent: Page/Page column 40

5
[ 300355-22-0 ]
[ 1003-61-8 ]
[ 1001419-48-2 ]

Yield	Reaction Conditions	Operation in experiment
74%	With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 3h;Product distribution / selectivity;	DIPEA (66 muL; 0.378 mmol) was added to a stirred solution of Example 1 Part D compound (80 mg; 0.270 mmol), <strong>[1003-61-8]2-amino-5-formylthiazole</strong> (43.3 mg; 0.338 mmol) and HOAt (44.0 mg; 0.324 mmol) in DMF (1.0 mL). EDAC (62.0 mg; 0.324 mmol) was added. After 3 h at RT, the reaction mixture was partitioned between EtOAc (8 mL) and H2O (8 mL). The organic phase was washed with 1N aqueous HCl (5 mL), sat. aqueous NaHCO3 (5 mL) and brine (5 mL), dried (MgSO4) and concentrated in vacuo. The crude product was chromatographed (SiO2; continuous gradient from 0 to 100% EtOAc in hexanes over 11 min, hold at 100% EtOAc for 4 min) to give Part A compound (81 mg; 74%) as a foam.

Reference： [1]Patent: US2008/9465,2008,A1 .Location in patent: Page/Page column 59

6
[ 32284-60-9 ]
[ 68-12-2 ]
[ 1003-61-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5518 - 5522

7
[ 1003-61-8 ]
[ 24424-99-5 ]
[ 391668-77-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In tetrahydrofuran; at 20℃; for 12h;	[0337] To a solution of 1.0 g of <strong>[1003-61-8]2-aminothiazole-5-carbaldehyde</strong> in 20 ml of THF was added 2.5 g of DIBOC and 1.4 g of DMAP at room temperature, and the mixture was stirred for 12 hours. Water was added to the mixture, and the mixture was extracted with EtOAc. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure, and the resulting crude product was purified by silica gel column chromatography to give 600 mg of t-butyl (5-formylthiazole-2-yl)carbamate (FAB-MS m/z: 229 (M++1)).
	In dichloromethane; at 20℃;	Compound 75 was prepared from commercially available <strong>[1003-61-8]2-aminothiazole-5-carbaldehyde</strong> by a standard procedure ((BOC)2O, DCM, room temperature).
	With dmap; In tetrahydrofuran; at 0 - 20℃; for 1h;	Step a. To a solution of <strong>[1003-61-8]2-aminothiazole-5-carbaldehyde</strong> (3.9 mmol) in THF (10 ml) was added DMAP (5.85 mmol) and (BOC)20 (5.85 mmol) at 0C. The reaction mixture was stirred at rt for 1 h. The resulting reaction mixture was poured into water (50 ml) and extracted with EtOAc (3 x 100 ml). The combined organic phase was collected, dried over Na2SC>4, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (40% EtOAc in hexane) yielding tert-butyl (5-formylthiazol-2-yl) carbamate (2.63 mmol). This material was used directly for the next step without further purification. MS: ES+ 229.05.

Reference： [1]Patent: WO2005/35541,2005,A1 .Location in patent: Page/Page column 13
[2]Patent: US2003/232860,2003,A1 .Location in patent: Page 21
[3]Patent: US2007/167435,2007,A1 .Location in patent: Page/Page column 46
[4]Patent: WO2016/46530,2016,A1 .Location in patent: Page/Page column 129

8
[ 1003-61-8 ]
[ 681143-32-8 ]
[ 681142-60-9 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃;	Example 3 [ 2- (2-HYDROXY-3, 3-DIMETHYL-BUTYRYLAMINO)-PENTANOIC ACID (5-FORMYL-THIAZOL-2-YL)-AMIDE] A mixture of (S, [S)-2- (2-HYDROXY-3, 3-DIMETHYL-BUTYRYLAMINO)-PENTANOIC] acid (1.09 g, 4.71 [MMOL),] [2-AMINO-THIAZOLE-5-CARBALDEHYDE] (0.606 g, 4.71 [MMOL),] HOBt (0.763 g, 5.65 [MMOL),] EDC. [HCI] (1.348 g, 7.07 mmol), and triethylamine (2.7 [ML,] 18.84 [MMOL)] in methylene chloride (50 [ML)] was stirred at room temperature overnight. The mixture was quenched with water, extracted with methylene chloride. The organic layer was washed with diluted HCI, separated, dried and concentrated. The residue was purified by silica gel column chromatography using 2% methanol in methylene chloride as eluent to give the title compound (505 mg) as a yellow solid.

Reference： [1]Patent: WO2004/33439,2004,A1 .Location in patent: Page 65

9
[ 1003-61-8 ]
[ 464192-28-7 ]

Yield	Reaction Conditions	Operation in experiment
69.13%	With tert.-butylnitrite; copper(I) bromide; In acetonitrile; at 25℃; for 5h;Inert atmosphere;	Under N2 protection,250mLIn a two-necked flask, tert-butyl nitrite (4.8 g, 47 mmol) and copper bromide (8.2 g, 40 mmol) and anhydrous acetonitrile (180 mL) were added, and the mixture was stirred at 25 C for 0.5 h.The compound <strong>[1003-61-8]2-aminothiazole-5-carbaldehyde</strong> (4.0 g, 31 mmol) was dissolved in anhydrous acetonitrile (30 mL) and slowly added dropwise to the above solution.The reaction was stirred at 25 C for 12.0 h. concentrate,Add ethyl acetate (200 mL),The organic layer was washed once with saturated brine (60 mL).Dry anhydrous sodium sulfate (20g), concentrated,4.12 g of a red solid were obtained in a yield: 69.13%.
	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 20℃; for 4h;	2-Amino-1, 3-THIAZOLE-5-CARBOXALDEHYDE (13.78 g, 0.108 mol, 1 eq) in acetonitrile (200 mL) (SLURRY) was added portionwise to a stirred suspension of CuBr2 (36.03 g, 0.129 mol) and t-butyl nitrite (19 mL, 0.161 mL) in acetonitrile (550 mL). The reaction was stirred at room temperature for 4 hours then evaporated to give a solid. This was treated with ethyl acetate (400 mL) and 2M HCI (400 mL). Water (200 mL), brine (100 mL) and ethyl acetate (200 mL) were added. The phases were separated. The aqueous phase was extracted with ethyl acetate (250 mL). The combined organic layers were dried (MGS04) and evaporated to give the title compound. 'H NMR (CDCI3) : 8 9.97 (1H, s), 8.19 (1H, s)
		Compounds 85 and 86 were synthesized by using the materials that have a substituent corresponding to these compounds, according to the following production scheme.

Reference： [1]Patent: CN104744446,2019,B .Location in patent: Paragraph 1729; 1741-1742
[2]Patent: WO2004/37818,2004,A1 .Location in patent: Page 69
[3]Patent: US2011/190299,2011,A1 .Location in patent: Page/Page column 20

10
[ 1003-61-8 ]
[ 101-83-7 ]
[ 859523-71-0 ]

Yield	Reaction Conditions	Operation in experiment
		Example 252; 1, 1-Dicyclohexyl-3- 5-formyl-thiazol-2-yl)-urea; 2-Amino-5-formylthiazole (215 mg, 1.67 mmol), carbonyldiimidazole (275 mg, 1.70 mmol) and a catalytic amount of DMAP were heated together in 5 mL THF at 40 C for 2h. To this solution was added dicyclohexylamine (0.34 mL, 1.70 mmol) and the reaction mixture was stirred for an additional 6 h at room temperature. The reaction mixture was concentrated and the crude product was purified by flash chromatography (silica, CH2CI2-EtOAc, 4: 1) to obtain 1, 1-dicyclohexyl-3- (5-formyl-thiazol-2-yl)-urea. HPLC-MS: m/z 336 (M+1).

Reference： [1]Patent: WO2005/66145,2005,A1 .Location in patent: Page/Page column 185-186

11
[ 1003-61-8 ]
[ 252662-37-6 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride; In toluene;	B. Preparation of 2-acetamido-thiazol-5-ylcarboxaldehyde To a suspension of 2-amino-thiazol-5-ylcarboxaldehyde (5.0 g, 39 mmol) in toluene (500 mL) was added acetic anhydride (11.0 mL, 117 mmol). The mixture was heated to 110 C. for 5 hours. Upon cooling to room temperature, a solid precipitated out of the solution. The reaction mixture was concentrated under vacuum to give 2-acetamido-thiazol-5-ylcarboxaldehyde as a light brown colored solid (6.5 g, 98%, C6H6N2O2S, MS m/e 171 (M+H)+).

Reference： [1]Patent: US6407124,2002,B1

12
[ 1003-61-8 ]
[ 203519-37-3 ]
[ 936845-85-1 ]

Yield	Reaction Conditions	Operation in experiment
42%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; for 7h;Heating / reflux;	In a dry 100 mL round bottom flask were combined intermediate 19 (2.8 g, 8.9 mmol), 2-amino-thiazole-5-carbaldehyde (1.4 g, 10.7 mmol), cesium carbonate (8.7 g, 26.7 mmol), Xantphos (1.03 g, 1.8 mmol) and tris(dibenzylideneacetone) dipalladium (0.82 g, 0.89 mmol). Reactants were diluted with dioxane (40 mL), flushed with argon and refluxed for 7 h. Reaction was then diluted with EtOAc and filtered. Solvents were then removed and resulting residue purified via column chromatography (silica gel) to provide title intermediate as yellow powder (1.5 g, 42%).[0130] 1H NMR (500 MHz, DMSO-d6): d 1.42 (s, 9H), 2.42 (s, 3H), 3.42 (m, 4H), 3.54 (m, 4H), 6.10 (s, IH), 8.30 (s, IH), 9.85 (s, IH), 11.90 (s, IH). MS (ES+): m/z 405 (M+H)+.

Reference： [1]Patent: WO2007/56023,2007,A2 .Location in patent: Page/Page column 49

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Technical Information

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Historical Records

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P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 1003-61-8 ] {[proInfo.proName]}

Quality Control of [ 1003-61-8 ]

Related Doc. of [ 1003-61-8 ]

Product Details of [ 1003-61-8 ]

Calculated chemistry of [ 1003-61-8 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1003-61-8 ]

Application In Synthesis of [ 1003-61-8 ]

[ 1003-61-8 ] Synthesis Path-Upstream 1~1

[ 1003-61-8 ] Synthesis Path-Downstream 1~12

Technical Information

Related Functional Groups of [ 1003-61-8 ]

Aldehydes

Amines

Related Parent Nucleus of [ 1003-61-8 ]

Thiazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 1003-61-8 ]

Related Parent Nucleus of
[ 1003-61-8 ]