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[ CAS No. 89-77-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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2D 3D

Chemical Structure| 89-77-0

Chemical Structure| 89-77-0

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Quality Control of [ 89-77-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 89-77-0 ]

SDS Specification

Alternatived Products of [ 89-77-0 ]

Product Citations

Product Details of [ 89-77-0 ]

CAS No. :	89-77-0	MDL No. :	MFCD00007778
Formula :	C₇H₆ClNO₂	Boiling Point :	No data available
Linear Structure Formula :	NH₂C₆H₃(Cl)CO₂H	InChI Key :	JYYLQSCZISREGY-UHFFFAOYSA-N
M.W :	171.58	Pubchem ID :	66646
Synonyms :

Calculated chemistry of [ 89-77-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	42.82
TPSA :	63.32 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.22
Log Po/w (XLOGP3) :	1.57
Log Po/w (WLOGP) :	1.63
Log Po/w (MLOGP) :	0.48
Log Po/w (SILICOS-IT) :	1.14
Consensus Log Po/w :	1.21

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.23
Solubility :	1.01 mg/ml ; 0.00588 mol/l
Class :	Soluble
Log S (Ali) :	-2.51
Solubility :	0.53 mg/ml ; 0.00309 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.02
Solubility :	1.63 mg/ml ; 0.00948 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.06

Safety of [ 89-77-0 ]

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

Application In Synthesis of [ 89-77-0 ]

* 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 [ 89-77-0 ]
Downstream synthetic route of [ 89-77-0 ]

[ 89-77-0 ] Synthesis Path-Upstream 1~5

1
[ 57-13-6 ]
[ 89-77-0 ]
[ 13165-35-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 200℃; for 1 h;	Step A: Preparation of 7-chloro-1H-quinazoline-2,4-dione. A mixture of 2-amino-4-chlorobenzoic acid (2.00 g, 11.6 mmol) and urea (2.80 g, 46.6 mmol) was heated to 200° C. for 1 h. The mixture was allowed to cool to room temperature and the resulting mass was triturated well with water. The product was collected by filtration (2.30 g, 100percent). The MS and NMR data are in agreement with those that have been previously described: Organic Process Research and Development, 2003, 7, 700-706. ¹H NMR (600 MHz, DMSO-d₆): 12.00 (br s, 2H), 8.59-8.53 (m, 1H), 7.93-7.80 (m, 2H).

Reference： [1] Patent: US2010/204226, 2010, A1, . Location in patent: Page/Page column 22
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 15, p. 7268 - 7274
[3] Tetrahedron, 1997, vol. 53, # 25, p. 8457 - 8478
[4] Patent: DE931845, 1952, ,
[5] Pharmaceutical Chemistry Journal, 1987, vol. 21, # 7, p. 478 - 483[6] Khimiko-Farmatsevticheskii Zhurnal, 1987, vol. 21, # 7, p. 802 - 807
[7] Journal of Medicinal Chemistry, 2014, vol. 57, # 7, p. 3075 - 3093
[8] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5141 - 5156

2
[ 89-77-0 ]
[ 13165-35-0 ]

Reference： [1] Journal of the Chemical Society, 1948, p. 1759,1765
[2] Patent: US5688803, 1997, A,
[3] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 8, p. 824 - 829

3
[ 590-28-3 ]
[ 89-77-0 ]
[ 13165-35-0 ]

Reference： [1] Chinese Chemical Letters, 2012, vol. 23, # 4, p. 431 - 433

4
[ 917-61-3 ]
[ 89-77-0 ]
[ 13165-35-0 ]

Reference： [1] Patent: US6344559, 2002, B1, . Location in patent: Page column 4

5
[ 89-77-0 ]
[ 208465-21-8 ]

Reference： [1] Patent: CN106243046, 2016, A,

[ 89-77-0 ] Synthesis Path-Downstream 1~2

1
[ 89-77-0 ]
[ 1499-21-4 ]
[ 5900-59-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With ammonium hydroxide; triethylamine; In dichloromethane;	Reference example 1: 2-amino-4-chlorobenzamide 4-Chloroanthranilic acid (75 g, 0.437 mol) was suspended in dichloromethane (1.09 1). To this suspension, triethylamine (73 ml, 0.524 mol) and diphenylphosphoryl chloride (141 g, 0.524 mol) were added successively, and the mixture was stirred at room temperature for 1 hour. Then, 28percent aqueous ammonia (44 ml) was added, and the mixture was further stirred at room temperature for 2 hours. After completion of the reaction, the reaction solution was filtrated, the filtrated crude crystal was washed with methanol to give 51.0 g (yield 68percent) of the title compound as yellow crystal.

Reference： [1]Patent: EP1229025,2002,A1

2
[ 89-77-0 ]
[ 5900-59-4 ]

Yield	Reaction Conditions	Operation in experiment
88%		To a solution of 2-amino-4-chlorobenzoic acid 11 (3.4 g,20 mmol) and HOBt (3.0 g, 22 mmol) in DMF (50 mL) was addedEDCI (4.6 g, 24 mmol). The mixture was stirred at rt for 2 h. Theresulting solution was cooled to 0 C, then 25% ammonia solution(20 mL) was added. The mixture was warmed to ambient temperatureand stirred for 1 h. The reaction mixture was poured intocrushed ice, filtered and washed with water to give 12 (3.0 g, 88%yield) as gray solid. 1H NMR (400 MHz, DMSO-d6) delta: 7.77 (s, 1H),7.54 (d, J = 8.5 Hz, 1H), 7.14 (s, 1H), 6.82 (s, 2H), 6.74 (d, J = 2.1 Hz,1H), 6.49 (dd, J = 8.5, 2.1 Hz, 1H). 13C NMR (101 MHz, DMSO-d6) delta:170.90, 151.98, 136.78, 131.06, 115.55, 114.45, 112.86 ppm. MS(ESI APCI) m/z 171.0 [M+H]+.
87.6%		Method I: 2-Amino-4-chlorobenzamide (ii-b) To a mixture of 2-amino-4-chlorobenzoic acid (3.42 g, 20 mmol) in DMF (45 mL) was added HOBt (2.70 g, 20 mmol). After stirring for 10 min, EDC hydrogen chloride (3.82 g, 20 mmol) was added to the mixture. The resulted mixture was stirred at room temperature for 2 h. NH4OH (28%, 5 mL) was added at 0 C. with vigorous stirring. After addition, the mixture was stirred at room temperature for another 2 h. The reaction mixture was added to water (200 mL) dropwise with stirring, then a precipitate formed. The precipitate was collected and dried in vacuo to give 2.98 g of ii-b as a grey solid (87.6% yield). LCMS m/z=171.0 (M+1), 173.0 (M+3) (Method B) (retention time=1.39 min). 1H NMR (400 MHz, DMSO-d6): delta 7.27 (d, J=9.6 Hz, 1H), 6.68 (d, J=2.4 Hz, 1H), 6.60 (dd, J=8.4, 2.0 Hz, 1H), 5.50-5.82 (m, 4H).
87.6%		HOBt (2.70 g, 20 mmol) was added to a mixture of 2-amino-4-chlorobenzoic acid (3.42 g, 20 mmol) in DMF (45 mL).After stirring for 10 minutes, EDC hydrogen chloride (3.82 g, 20 mmol) was added to the mixture. The resulting mixture was stirred at room temperature for 2 hours.NH 4 OH (28%, 5 mL) was added at 0 C. with vigorous stirring.After the addition, the mixture was stirred at room temperature for a further 2 hours.The reaction mixture was added dropwise to water (200 mL) with stirring, and a precipitate was formed. The precipitate was collected and dried in vacuo to give 2.98 g of ii-b as a gray solid (yield 87.6%).

66%

With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide; at 20℃; for 96h;

[00393] Step A: To solution of 2-amino-4-chlorobenzoic acid (4.4 g, 25.8 mmol) in degassed DMF (75 mL) were added successively HOBt (4.19 g, 31 mmol), DIEA (5.4 mL, 31 mmol), EDCI (5.37 g, 28 mmol), and 2N NH3MeOH (18 mL, 36 mmol), and the solution was stirred at rt for 4 d. The mixture was concentrated under reduced pressure and the residue was partitioned between H2O (200 mL) and DCM (200 mL). The separated aqueous phase was extracted with DCM (2 X 200 mL) and the combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 10-50% EtOAc/hexanes to afford 2-amino-4-chlorobenzamide as a solid (2.91 g, 660Zo)-1H NMR (300 MHz, DMSO-J6) delta 6.50 (dd, J= 8.48, 2.26 Hz, 1 H), 6.75 (d, J = 2.26 Hz, 1 H), 6.84 (br s, 2 H), 7.18 (br s, 1 H), 7.48 - 7.63 (m, 1 H), 7.80 (br s, 1 H).

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 1361 - 1375
[2]Patent: US2015/307477,2015,A1 .Location in patent: Paragraph 1473
[3]Patent: JP6121658,2017,B2 .Location in patent: Paragraph 1063; 1064; 1065
[4]Patent: WO2010/99379,2010,A1 .Location in patent: Page/Page column 142
[5]ARKIVOC,2012,vol. 2012,p. 198 - 213
[6]Journal of Agricultural and Food Chemistry,2015,vol. 63,p. 6883 - 6889
[7]Biochemistry,2017,vol. 56,p. 6491 - 6502
[8]Chinese Chemical Letters,2019,vol. 30,p. 1207 - 1213
[9]Phosphorus, Sulfur and Silicon and the Related Elements,2019

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Arndt-Eistert Homologation ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bouveault-Blanc Reduction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Catalytic Hydrogenation ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? Ester Cleavage ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hunsdiecker-Borodin Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? Mannich Reaction ? Passerini Reaction ? Petasis Reaction ? Preparation of Alkylbenzene ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Carboxylic Acids ? Reactions with Organometallic Reagents ? Schmidt Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction ? Vilsmeier-Haack Reaction

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