[ CAS No. 4664-01-1 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 4664-01-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4664-01-1 ]

SDS Specification

Alternatived Products of [ 4664-01-1 ]

Product Details of [ 4664-01-1 ]

CAS No. :	4664-01-1	MDL No. :	MFCD00013439
Formula :	C₇H₄N₂O₂	Boiling Point :	-
Linear Structure Formula :	C₅H₃N(CO)₂NH	InChI Key :	SJSABZBUTDSWMJ-UHFFFAOYSA-N
M.W :	148.12	Pubchem ID :	72926
Synonyms :

Calculated chemistry of [ 4664-01-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.61
TPSA :	59.06 ?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) :	-7.45 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.59
Log Po/w (XLOGP3) :	-0.35
Log Po/w (WLOGP) :	-0.42
Log Po/w (MLOGP) :	0.06
Log Po/w (SILICOS-IT) :	1.05
Consensus Log Po/w :	0.19

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.94
Solubility :	16.9 mg/ml ; 0.114 mol/l
Class :	Very soluble
Log S (Ali) :	-0.43
Solubility :	55.3 mg/ml ; 0.373 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.38
Solubility :	0.61 mg/ml ; 0.00412 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.37

Safety of [ 4664-01-1 ]

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

Application In Synthesis of [ 4664-01-1 ]

* 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 [ 4664-01-1 ]
Downstream synthetic route of [ 4664-01-1 ]

[ 4664-01-1 ] Synthesis Path-Upstream 1~1

1
[ 4664-01-1 ]
[ 14208-83-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 8, p. 2061 - 2071
[2] Australian Journal of Chemistry, 1993, vol. 46, # 7, p. 987 - 993

[ 4664-01-1 ] Synthesis Path-Downstream 1~5

1
[ 4664-01-1 ]
[ 7579-20-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With bromine; sodium hydroxide; In water; at 90℃; for 0.666667h;Cooling with ice;	Step 1 To 10percent aqueous sodium hydroxide solution (100 mL) was added bromine (1.93 mL, 38.6 mmol) under ice-cooling, and 1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione (5.20 g, 35.1 mmol) was subsequently added. 10percent-Aqueous sodium hydroxide solution (60 mL) was added to the reaction mixture, and the mixture was stirred with heating at 90° C. for 40 min. After allowing to cool to room temperature, 50percent sulfuric acid was added to adjust the reaction mixture to pH 3. The precipitated insoluble material was collected by filtration, and the solid was washed with water to give 3-aminoisonicotinic acid as a pale-yellow powder (5.00 g, 100percent). 1H-NMR (200 MHz, DMSO-d6) delta: 7.46 (1H, d, J=5.1 Hz), 7.73 (1H, d, J=5.1 Hz), 8.21 (1H, s).
68.33%		NaOH (10percent aqueous, 640 ml) was cooled to 7° C. and bromine (15 ml, 286.82 mmol) added dropwise. Pyrrolo[3,4-c]pyridine-1,3-dione (41.711 g, 281.6 mmol) was then added to the reaction mixture before it was heated to 80° C. for 30 minutes. After this time the reaction was allowed to warm to 37° C. and the pH modified to 5.5 by the addition of acetic acid (70 ml). A suspension formed that was removed by filtration and washed with 20 ml of ice cold methanol to give the title compound (26.58 g, 68.33percent) in a suitably clean form to be used without any further purification. m/z (LC-MS, ESP): 139 [M+H]+, R/T=0.72 mins.
67%		Bromine (3. 5 ml, 69.0 mmol) was added to a solution of 10 percent aqueous sodium hydroxide (120 ml) at 0 C to give a pale yellow solution. To this solution was added 3,4-pyridinedicarboximide (10 g, 67. 5 mmol) and the reaction was heated at 80 C for 45 min. The reaction was cooled in a water bath and acidified by the addition of acetic acid (12. 5 ml) causing precipitation. The solid was collected, rinsed with water(50 ml), thenMeOH(50 ml) and dried to give the title compound as a beige solid (6.28 g, 67 percent).1H NMR (360 MHz, DMSO)5 8. 06 (1H, s), 7.60(1H, d,J5. 1), 7.34(1H, d,J5. 1), 3.19 (2H, brs). M/z (ES+) 139 (M+H+).

64%		Following the procedures of Zhou et al (2001) Bioorg. Med. Chem. Lett.9(8):2061-2071, bromine (1.22 ml, 23.9 mmol) was slowly added to a cooled (50C) 2.5N solution of NaOH (60 ml, 150 mmol) and after stirring for 5 minutes pyrrolo[3,4-c]pyridine- 1,3-dione (3.5 g, 23.6 mmol) was added. The temperature was raised to 8O0C and the mixture was stirred for 1 hour before being cooled to ambient temperature. Acetic acid (5.9 ml, 98.3 mmol) was cautiously added (N.B.: gas evolution) and the solution stirred for 10 minutes whereby a precipitate formed that was collected by filtration. The solid was washed with water (20 ml) and MeOH (20 ml) then dried to afford the title compound as a yellow solid (2.1 g, 64percent).
62%	With sodium hydroxide; bromine; In water; at 0 - 80℃; for 0.75h;	A solution of10percent aqueousNaOH (416 mL) was cooled to0 C and treated with bromine (28.2 g 176 mmol) portionwise via pipette while keeping the temperature below 5 C. To this mixture was added 3,4-pyridinedicarboximide (25.78 g, 174mmol), and the cooling bath was removed. The reaction was heated to80 C for 45 min, then allowed to cool in an ice bath. When the temperature fell to 60 C, the dropwise addition of HOAc (50 mL) was started. Cooling was continued until the temperature reached 15 C. A yellow precipitate formed. The solid was filtered, rinsed with water, then dried under vacuum to give 14.9 g of product (108 mmol,62percent). 1NMR IS-MS, m/e 139(m+1)
57%	With bromine; In sodium hydroxide;	Preparation 18 3-Aminopyridine-4-carboxylic acid To an ice cold mixture of 3,4-pyridinedicarboximide (5.2 g, 35.11 mmol) in 10percent sodium hydroxide (85 mL) was added bromine (1.84 mL, 35.8 mmol), dropwise. The resulting solution was heated to 80° C. for 1 hour, cooled on ice, and the acidity was carefully adjusted to pH 5.5 with acetic acid. The precipitate was collected, washed well with water and air dried to afford 3-aminopyridine-4-carboxylic acid (2.74 g, 57percent). NMR (DMSO d6) delta8.20 (s, 1H), 7.72 (d, J=5 Hz, 1H), 7.45 (d, J=5 Hz, 1H). The material was used without purification.
57%		Step A: 3-Aminoisonicotinic acid: 2H-Pyrrolo[3,4-c]pyridine-1,3-dione (204.16 g, 1378.4 mmol) was dissolved in 10percent NaOH (3.3 L) and the solution was cooled to an internal temperature of 7° C. (ice/salt bath). Bromine (73.424 mL, 1433.5 mmol) was added dropwise while maintaining the internal temperature below 10° C. After completion of the addition, the reaction was heated to an internal temperature of 80-85° C. for 90 minutes. The reaction mixture was cooled to 20-30° C. in an ice bath then acetic acid (323.21 mL, 5651.2 mmol) was added dropwise. The reaction was stirred and cooled to 5° C. The solids were collected by vacuum filtration, washed with cold water then air-dried to provide the product (108.86 g, 57percent).
57%	With bromine; In sodium hydroxide;	Preparation 18 3-Aminopyridine-4-carboxylic acid To an ice cold mixture of 3,4-pyridinedicarboximide (5.2 g, 35.11 mmol) in 10percent sodium hydroxide (85 mL) was added bromine (1.84 mL, 35.8 mmol), dropwise. The resulting solution was heated to 80° C. for 1 hour, cooled on ice, and the acidity was carefully adjusted to pH 5.5 with acetic acid. The precipitate was collected, washed well with water and air dried to afford 3-aminopyridine-4-carboxylic acid (2.74 g, 57percent). 1H NMR (DMSO d6) delta8.20 (s,1 H), 7.72 (d, J=5 Hz, 1 H), 7.45 (d, J=5 Hz, 1 H). The material was used without purification.
		Preparation 5 Step 1: 3,4 Pyridine-dicarboximide (10.0 g, 67.5 [MMOL)] was dissolved in 10percent aqueous [NAOH] (162 g) and the solution was cooled to an internal temperature [OF 7 OC] in an ice-salt bath. Bromine (3.6 ml ; 70 [MMOL)] was added dropwise. After the addition, the solution was heated for 45 min at a bath temperature of 80-85 [°C.] The yellow solution was then cooled to an internal temperature of 37 [°C,] and [GLACIAL ACOH] (17 ml) were added dropwise to a pH of 5.5. The resulting mixture was refrigerated overnight. The solid formed was filtered and washed with water (5 ml) and CH30H (5 [ML).] The reaction yielded 6.35 g. of product, m. p. 280-285 [°C] (decomp. ).
	With sodium hydroxide; bromine; In water; at 0 - 85℃; for 0.75h;	3,4 Pyridine-dicarboximide 288 (10.0 g; 67.5 mmoles) was dissolved in 162 g. of 10percent aqueous NaOH and the solution was cooled to an internal temperature of 70C in an ice-salt bath. Bromine (3.6 ml; 70 mmoles) was added dropwise. After the addition, the solution was heated for 45 minutes at a bath temperature of 80-85 0C. The yellow solution was then cooled to an internal temperature of 37 0C, then 17 ml of glacial acetic acid were added dropwise to a pH of 5.5. The resulting mixture was saved overnight in a refrigerator. The solid formed was filtered and washed with 5 ml of water and 5 ml of methanol. The reaction yielded 6.35 g. of product 289 melting at 280-285 0C (decomp.).

Reference： [1]Patent: US2015/329556,2015,A1 .Location in patent: Paragraph 1612-1614
[2]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 2061 - 2071
[3]Australian Journal of Chemistry,1993,vol. 46,p. 987 - 993
[4]Tetrahedron Letters,1993,vol. 34,p. 6225 - 6228
[5]Patent: US2006/199804,2006,A1 .Location in patent: Page/Page column 29
[6]Patent: WO2005/49613,2005,A1 .Location in patent: Page/Page column 38
[7]Patent: WO2008/24725,2008,A1 .Location in patent: Page/Page column 67
[8]Patent: WO2005/49604,2005,A2 .Location in patent: Page/Page column 69
[9]Journal of Medicinal Chemistry,2017,vol. 60,p. 6942 - 6990
[10]Patent: US5962457,1999,A
[11]Patent: US2007/49603,2007,A1 .Location in patent: Page/Page column 78; 30
[12]Patent: US6323208,2001,B1
[13]Patent: WO2004/831,2003,A1 .Location in patent: Page 22
[14]Patent: WO2008/108957,2008,A2 .Location in patent: Page/Page column 95

2
[ 4664-01-1 ]
[ 152398-05-5 ]

Reference： [1]Australian Journal of Chemistry,1993,vol. 46,p. 987 - 993
[2]Patent: WO2008/108957,2008,A2

3
[ 4664-01-1 ]
MeOH (NH₃) [ No CAS ]
[ 152398-05-5 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; In tetrahydrofuran; methanol; sodium hydroxide; water; acetic acid;	EXAMPLE 29 3,4 Pyridine-dicarboximide 288 (10.0 g; 67.5 mmoles) was dissolved in 162 g. of 10% aqueous NaOH and the solution was cooled to an internal temperature of 7 C. in an ice-salt bath. Bromine (3.6 ml; 70 mmoles) was added dropwise. After the addition, the solution was heated for 45 minutes at a bath temperature of 80-85 C. The yellow solution was then cooled to an internal temperature of 37 C., then 17 ml of glacial acetic acid were added dropwise to a pH of 5.5. The resulting mixture was saved overnight in a refrigerator. The solid formed was filtered and washed with 5 ml of water and 5 ml of methanol. The reaction yielded 6.35 g. of product 289 melting at 280-285 C. (decomp.). Solid Compound 289 (9.5 gr.; 69 mmoles) was carefully added in three aliquots to a slurry of lithium aluminum hydride (9.5 gr.; 250 mmoles) in 200 ml of dry tetrahydrofuran. The resulting hot mixture was stirred at room temperature for two days. After cooling in an ice bath, the reaction was quenched with very careful sequential dropwise addition of 10 ml of water, followed by 10 ml of 15% aqueous NaOH, then by 30 ml of water. The resulting solid was filtered through a pad of Celite and washed several times with THF. The oil obtained after evaporation of the solvent, solidified on standing. The reaction mixture was purified by flash chromatography on silica gel using 5%MeOH(NH3)/EtOAc as eluent yielding 6.21 (72%) of Compound 290. LC-MS: m/z=125 (M+1).

Reference： [1]Patent: US2003/45519,2003,A1

4
[ 4664-01-1 ]
3-Aminopyridine-4-carboxvlic acid [ No CAS ]
[ 7579-20-6 ]

Yield	Reaction Conditions	Operation in experiment
57%	With bromine; In sodium hydroxide;	Preparation 18 3-Aminopyridine-4-carboxvlic acid To an ice cold mixture of 3,4-pyridinedicarboximide (5.2 g, 35.11 mmol) in 10percent sodium hydroxide (85 mL) was added bromine (1.84 mL, 35.8 mmol), dropwise. The resulting solution was heated to 80°C for 1 hour, cooled on ice, and the acidity was carefully adjusted to pH 5.5 with acetic acid. The precipitate was collected, washed well with water and air dried to afford 3-aminopyridine4-carboxylic acid (2.74 g, 57percent). NMR (DMSO d6) delta 8.20 (s, 1 H), 7.72 (d, J = 5 Hz, 1 H), 7.45 (d, J = 5 Hz, 1 H). The material was used without purification.

Reference： [1]Patent: EP807633,1997,A2

5
[ 4664-01-1 ]
[ 5655-00-5 ]

Yield	Reaction Conditions	Operation in experiment
62%		Step lTo a solution of compound [137] (3 g, 20.2 mmol, leq) in glacial acetic acid (30 ml), Zn dust (5.26 g, 81.0 mmol, 4 eq.) was added and the reaction mixture was refluxed at 100 C for 4 h. The reaction mixture was cooled to room temperature and the solvent was evaporated. The reaction mass was made basic with aqueous NaHC03 to pH 8 and extracted with chloroform. The aqueous layer was concentrated and further extracted with chloroform. The combined organic layer was dried over Na2S04 and evaporated to give [138] as a peach white solid (1.7 g, 62%).ESIMS: 135 (M+ + 1)

Reference： [1]Patent: WO2012/101654,2012,A2 .Location in patent: Page/Page column 72

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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. 4664-01-1 ] {[proInfo.proName]}

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[ 4664-01-1 ] Synthesis Path-Upstream 1~1

[ 4664-01-1 ] Synthesis Path-Downstream 1~5

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