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Chemical Structure| 89-77-0
Chemical Structure| 89-77-0
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Product Details of [ 89-77-0 ]

CAS No. :89-77-0 MDL No. :MFCD00007778
Formula : C7H6ClNO2 Boiling Point : -
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 Ų

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: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 [ 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   1~57

  • 1
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Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 8966 - 8970
  • 2
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YieldReaction ConditionsOperation in experiment
95% Microwave irradiation 10g of compound BB1, formamidine acetate 8g (1.3eq) into 100ml eggplant-shaped flask, uniformly mixed, the microwave reaction 4πη (60percent power). After cooling, 30ml of water was added, the solid was washed and filtered to give the BB2 compound 10g, yield 95percent.
88.1% at 120℃; for 16 h; 4-Chloro-2-aminobenzoic acid(10.26, 60.0mmol) and formamidine acetate (12.5g, 120.0mmol]Into the 250mL ethylene glycol monomethyl ether, heated to 120 ° C, insulation reaction 16h,Cooled to room temperature, concentrated to dryness under reduced pressure,Washed with 0.0lmol / L ammonia to neutral, filtered and dried to give an off-white solid of 7-chloro-3H-quinazolin-4-one in a yield of 88.1percent
Reference: [1] Patent: CN103570738, 2016, B, . Location in patent: Paragraph 0303; 0304; 0306
[2] Patent: CN103382182, 2016, B, . Location in patent: Paragraph 0272-0275
[3] Patent: WO2012/88712, 2012, A1, . Location in patent: Page/Page column 16
[4] MedChemComm, 2015, vol. 6, # 1, p. 222 - 229
  • 3
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YieldReaction ConditionsOperation in experiment
96.1% at 150℃; for 2 h; Examples 13 to 21:; The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the type of the anthranilic acid derivative was changed. The results are shown in Table 4.
90.7% at 130 - 160℃; for 5 h; At room temperature,Add p-chloroanthranilic acid (20 g, 116.56 mmol) to a 250 ml round bottom flask.Add formamide (50 mL, 1.26 mol),Heating to 130 ° C, and then heating up to 160 ° C when completely dissolved,The reaction was carried out for 5 h, and the reaction was completed by TLC. After cooling to room temperature, the reaction solution was poured into 400 ml of ice water and stirred.A large amount of solid is produced, suction filtered, dried, and recrystallized from ethanol to give an off-white intermediate 419.1g, yield 90.7percent,
87.7% at 130 - 190℃; for 4.5 h; A mixture of compound 0301(17.2 g, 100 mmol) and formamide (20 mL) was stirred at 130 0C for 30 minutes and to 190 0C for 4 hours. The mixture was allowed to cool to room temperature. It was then poured into a mixture of ice and water. The precipitate was isolated, washed with water and dried to give the title compound 0302 (15.8 g, 87.7percent). 1H NMR (DMSO-J6): δ 7.65 (dd, IH), 7.72 (d, IH), 8.12 (d, IH), 8.36 (s, IH).
87.7% at 130 - 190℃; for 4.5 h; Example 22Preparation of N1-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yl)-N5-hydroxyglutaramide (Compound 38)Step 22a. 7-Chloroquinazolin-4 (3H)-one (Compound 0302); A mixture of compound 0301 (17.2 g, 100 mmol) and formamide (20 mL) was stirred at 130° C. for 30 minutes and to 190° C. for 4 hours. The mixture was allowed to cool to room temperature. It was then poured into a mixture of ice and water. The precipitate was isolated, washed with water and dried to give the title compound 0302 (15.8 g, 87.7percent). 1H NMR (DMSO-d6): δ 7.65 (dd, 1H), 7.72 (d, 1H), 8.12 (d, 1H), 8.36 (s, 1H).
83% at 140℃; General procedure: To a three necked flask, substituted anthranilic acid (1 meq.) was added in excess of formamide (6 meq). The reaction mixture was then heated at 140 °C for 4-6 h. The reaction was monitored with thin layer chromatography and upon completion; ice was added to the reaction mixture. The resultant solid was filtered, washed with water, dissolved in ethyl acetate, dried over MgSO4 and concentrated to obtain the pure desired product. Where product did not precipitate on addition of ice, the reaction mixture was extracted with ethyl acetate, dried over MgSO4 and concentrated to obtain the desired quinazolin-4(3H)-one derivatives 1-9, 11-15, 17-21 and 23-25.The amino derivatives 10, 16 and 22 were prepared using the following general procedure:To a reaction flask, substituted nitroquinazolin-4(3H)-one derivative (0.3 g, 1.56 mmol) was added followed by addition of 6 mL ethyl acetate and SnCl2*2H2O (2.12 g, 9.42 mmol), then reaction mixture was refluxed for 8 h. The reaction mixture was cooled to room temperature and quenched with saturated sodium bicarbonate solution, followed by repeated extraction with ethyl acetate (3 .x. 50 mL). The organic layers were combined, dried over anhydrous MgSO4 and concentrated to obtain the desired amino substituted quinazolin-4(3H)-one derivatives 10, 16 and 22.The substituted anthranilic acid (1 g) was dissolved in excess acetic anhydride (10 mL) and the resulting reaction mixture was stirred at room temperature for 4-7 h. The reaction was monitored for completion using thin layer chromatography. The solvent was evaporated under vacuum and the resultant residue was stirred with ammonia solution for 7 h. Upon completion, the reaction mixture was extracted with ethyl acetate (3 .x. 10 mL), the organic extracts were combined, dried over MgSO4 and evaporated to obtain compounds 26-30, 31a and 32. The 2-methyl-8-nitroquinazolin-4(3H)-one intermediate (31a) was reduced to compound 31 using the same procedure as reported in Scheme 1 for the synthesis of compounds 10, 16 and 22.
19.1 g for 4 h; Reflux General procedure: 6,7-dimethoxyquinazolin-4(3H)-one (6a) was prepared accordingto a similar procedure of Luth and Lowe [62], with formamidein replace of formamidine acetate. Briefly, a solution of 5a(5 g, 25.4 mmol) in formamide (30 mL) was heated to reflux for 4 h,cooled to rt and poured onto ice-water, extracted with ethyl acetate,washed with brine and dried over Na2SO4, After removal of thesolvent, the residue was purified by silica gel column to give 6,7-dimethoxyquinazolin-4(3H)-one (6a) as a white solid (4.5 g, yield86percent). mp 310-312 °C (reference mp 300 °C [64]).

Reference: [1] Patent: EP1997812, 2008, A1, . Location in patent: Page/Page column 8
[2] Heterocyclic Communications, 2001, vol. 7, # 4, p. 337 - 340
[3] Patent: CN108484574, 2018, A, . Location in patent: Paragraph 0130; 0131; 0132
[4] Cell Chemical Biology, 2017, vol. 24, # 12, p. 1490 - 11,1500
[5] Patent: WO2008/33747, 2008, A2, . Location in patent: Page/Page column 129
[6] Patent: US2009/111772, 2009, A1, . Location in patent: Page/Page column 73
[7] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 264 - 273
[8] Medicinal Chemistry Research, 2013, vol. 22, # 9, p. 4096 - 4109
[9] Journal of the American Chemical Society, 1946, vol. 68, p. 1305
[10] Huaxue Xuebao, 1956, vol. 22, p. 335,336[11] Scientia Sinica (English Edition), 1958, vol. 7, p. 1035,1036
[12] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
[13] Journal of the Chemical Society, 1947, p. 890,894
[14] Patent: US2005/165032, 2005, A1, . Location in patent: Page/Page column 9
[15] Patent: US2008/300248, 2008, A1, . Location in patent: Page/Page column 7
[16] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3851 - 3855
[17] Biochemistry, 2017, vol. 56, # 49, p. 6491 - 6502
[18] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
  • 4
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  • [ 31374-18-2 ]
Reference: [1] Patent: US5952333, 1999, A,
  • 5
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  • [ 31374-18-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2002, vol. 38, # 7, p. 817 - 821
[2] Chemistry of Heterocyclic Compounds, 2002, vol. 38, # 7, p. 817 - 821
[3] Patent: EP1990337, 2008, A1, . Location in patent: Page/Page column 11
  • 6
  • [ 6313-33-3 ]
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Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 19, p. 3860 - 3873
  • 7
  • [ 64392-62-7 ]
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Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 5, p. 616 - 620
  • 8
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  • [ 2148-57-4 ]
Reference: [1] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1982, vol. 37, # 7, p. 907 - 911
[2] Patent: WO2012/88712, 2012, A1,
[3] Patent: WO2014/145512, 2014, A2,
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3851 - 3855
  • 9
  • [ 89-77-0 ]
  • [ 2034-23-3 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 4, p. 735 - 742
  • 10
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  • [ 6625-94-1 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1987, vol. 21, # 7, p. 478 - 483[2] Khimiko-Farmatsevticheskii Zhurnal, 1987, vol. 21, # 7, p. 802 - 807
[3] Patent: DE931845, 1952, ,
[4] Journal of the Chemical Society, 1948, p. 1759,1765
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 7, p. 3075 - 3093
[6] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5141 - 5156
[7] Journal of Medicinal Chemistry, 2016, vol. 59, # 15, p. 7268 - 7274
[8] RSC Advances, 2017, vol. 7, # 36, p. 22360 - 22368
  • 11
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YieldReaction ConditionsOperation 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
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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
  • 13
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Reference: [1] Chinese Chemical Letters, 2012, vol. 23, # 4, p. 431 - 433
  • 14
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Reference: [1] Patent: US6344559, 2002, B1, . Location in patent: Page column 4
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YieldReaction ConditionsOperation in experiment
74% With pyridine In dichloromethane; acetonitrile at 50℃; for 2 h; Intermediate G: 7-chloro-1H-benzo[d][1,3]oxazine-2,4-dione
To a stirred solution of 2-amino-4-chloro benzoic acid (10 g, 0.058 mmol) in acetonitrile (60 mL, 1 M), was added pyridine (9.4 mL, 0.117 mmol, 2 equiv), and triphosgene (17.3 g, 0.058 mmol, 1 equiv) in dichloromethane (85 mL, 0.7 M). The orange reaction solution was heated at 50° C. for two hours then cooled to room temperature. The solution was diluted with water (50 mL), and the organic and aqueous layers were separated. The aqueous layer was washed with dichloromethane (3×50 mL), and the combined organic layers were washed once with brine (50 mL), and dried over magnesium sulfate. The solvent was removed in vacuo leaving a yellow solid. The solid was titrated with hexanes to yield 7-chloro-1H-benzo[d][1,3]oxazine-2,4-dione (9.1 g, 74percent) as a yellow solid.1H NMR (Acetone, 500 MHz): δ (ppm) 7.13-7.14 (1H, s), 7.28-7.30 (1H, d, J=8.5 Hz), 7.90-7.92 (1H, d, J=8.6 Hz), 11.84 (1H, bs).
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 17, p. 6928 - 6937
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2311 - 2319
[3] Patent: US9126978, 2015, B2, . Location in patent: Page/Page column 57; 58
[4] European Journal of Medicinal Chemistry, 1994, vol. 29, # 12, p. 925 - 940
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 10, p. 2295 - 2299
[6] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 31, p. 6883 - 6889
[7] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 2, p. 437 - 440
[8] Biochemistry, 2017, vol. 56, # 49, p. 6491 - 6502
[9] Chemical Biology and Drug Design, 2018, vol. 92, # 5, p. 1914 - 1919
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  • [ 40928-13-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 7, p. 1257 - 1263
[2] European Journal of Medicinal Chemistry, 1983, vol. 18, # 3, p. 241 - 247
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 8, p. 2075 - 2088
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  • [ 75-44-5 ]
  • [ 497-19-8 ]
  • [ 89-77-0 ]
  • [ 40928-13-0 ]
  • [ 252232-80-7 ]
Reference: [1] Patent: US6087368, 2000, A,
  • 18
  • [ 79-37-8 ]
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  • [ 40928-13-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 1, p. 138 - 147
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  • [ 2642-63-9 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 232,236
[2] Journal of the Chemical Society, 1947, p. 232,236
[3] Journal of the Chemical Society, 1947, p. 232,236
  • 20
  • [ 6280-88-2 ]
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Reference: [1] Chemical Biology and Drug Design, 2016, p. 710 - 723
[2] Journal of the American Chemical Society, 1954, vol. 76, p. 6336,6337
[3] Journal of the American Chemical Society, 1923, vol. 45, p. 1028
[4] Collection of Czechoslovak Chemical Communications, 1968, vol. 33, # 6, p. 1852 - 1872
[5] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
  • 21
  • [ 50-84-0 ]
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Reference: [1] Pharmaceutical Chemistry Journal, 1987, vol. 21, # 1, p. 34 - 45[2] Khimiko-Farmatsevticheskii Zhurnal, 1987, vol. 21, # 1, p. 38 - 49
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 171
  • 22
  • [ 5900-58-3 ]
  • [ 89-77-0 ]
Reference: [1] Patent: WO2018/144620, 2018, A1, . Location in patent: Paragraph 00426
  • 23
  • [ 66909-52-2 ]
  • [ 89-77-0 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1987, vol. 21, # 1, p. 34 - 45[2] Khimiko-Farmatsevticheskii Zhurnal, 1987, vol. 21, # 1, p. 38 - 49
  • 24
  • [ 34662-32-3 ]
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Reference: [1] Journal of the American Chemical Society, 1923, vol. 45, p. 1028
[2] Journal of the American Chemical Society, 1923, vol. 45, p. 1028
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Reference: [1] Journal of the American Chemical Society, 1923, vol. 45, p. 1028
[2] Journal of the American Chemical Society, 1923, vol. 45, p. 1028
  • 26
  • [ 6341-92-0 ]
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Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 1251,1254
  • 27
  • [ 5900-59-4 ]
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Reference: [1] Journal of the American Chemical Society, 1923, vol. 45, p. 1028
  • 28
  • [ 74-11-3 ]
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Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
  • 29
  • [ 5900-56-1 ]
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Reference: [1] Monatshefte fuer Chemie, 1901, vol. 22, p. 485
  • 30
  • [ 5900-55-0 ]
  • [ 89-77-0 ]
Reference: [1] Monatshefte fuer Chemie, 1901, vol. 22, p. 485
  • 31
  • [ 61680-22-6 ]
  • [ 89-77-0 ]
Reference: [1] Zhurnal Obshchei Khimii, 1953, vol. 23, p. 606,609; engl. Ausg. S. 629, 632
  • 32
  • [ 96385-49-8 ]
  • [ 89-77-0 ]
Reference: [1] Journal of the Chemical Society, 1945, p. 625,627
  • 33
  • [ 2909-38-8 ]
  • [ 89-77-0 ]
Reference: [1] Zhurnal Obshchei Khimii, 1953, vol. 23, p. 606,609; engl. Ausg. S. 629, 632
  • 34
  • [ 67-56-1 ]
  • [ 6341-92-0 ]
  • [ 5900-58-3 ]
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Reference: [1] Angewandte Chemie, 1981, vol. 93, # 10, p. 914 - 915
  • 35
  • [ 35112-28-8 ]
  • [ 89-77-0 ]
Reference: [1] Chemische Berichte, 1942, vol. 75, p. 1008,1014
  • 36
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  • [ 53449-14-2 ]
Reference: [1] Medicinal Chemistry Research, 2013, vol. 22, # 9, p. 4096 - 4109
[2] Patent: CN103570738, 2016, B,
[3] Patent: CN103382182, 2016, B,
[4] Patent: US2009/111772, 2009, A1,
[5] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
[6] Patent: CN108484574, 2018, A,
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YieldReaction ConditionsOperation in experiment
83% at -5℃; for 4.5 h; Reflux; Industrial scale 17.1g of 4-chloro-2-aminobenzoic acid (0.1mol), 100mL of methanol was added to the reaction vessel, stirred to dissolve, cooled to -5 ~ 0 ,Slowly added dropwise 10mL thionyl chloride, dropwise addition, remove the ice bath, slowly warmed to room temperature, stirred 0.5h, the reaction was warmed to reflux, the reaction 4h, steamed added 70mL methanol, the next set of applications, the raffinate Add ice water, add sodium bicarbonate to neutral, filter, the filter cake was dissolved with 100mL dichloromethane, filtered to give unreacted 4-chloro-2-amino benzoic acid 1.8g, can be applied directly to the next ester The methylene chloride layer was dried over 5 g of anhydrous sodium sulfate, filtered and the solvent was distilled off to obtain 15.4 g of methyl 4-chloro-2-aminobenzoate (2) in a yield of 83percent.
82% at 0 - 5℃; for 24 h; Reflux A single-mouth bottle was charged with 10 g of 2-amino-4-chlorobenzoic acid, 150 ml of methanol, cooled to 0 to 5 ° C, and 10.4 g of thionyl chloride was added dropwise thereto.After the addition was completed, the temperature was refluxed for 24 hrs. It was cooled to room temperature and concentrated under reduced pressure to remove methanol.Add 100 ml of ethyl acetate, 100 ml of 5percent sodium carbonate solution, stir, let stand, separate the aqueous layer, and wash the organic layer with 100 ml of water.Dry over anhydrous sodium sulfate and concentrate under reduced pressureMethyl 2-amino-4-chlorobenzoate 8.9 g, yield 82percent.
62%
Stage #1: With hydrogenchloride In water for 12 h; Reflux
Stage #2: With sodium hydroxide In water
Methyl 2-amino-4-chlorobenzoate; To a mixture of 2-amino-4-chlorobenzoic acid (150 g, 0.88 mol) in MeOH (2.6 L) was added cone. HCl (0.5 L, 16.5 mol) and the reaction mixture was allowed to stir at reflux. After 12 h, the reaction mixture was allowed to cool to rt and was concentrated. Water (0.5 L) was added to the residue and the solution basified with 10percent aqueous NaOH. The resulting precipitate was filtered to give methyl 2-amino-4-chlorobenzoate (101 g, 62percent).
Reference: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 17, p. 3248 - 3255
[2] Patent: CN106243046, 2016, A, . Location in patent: Paragraph 0047; 0052; 0053; 0073; 0074
[3] Patent: CN107778229, 2018, A, . Location in patent: Paragraph 0021
[4] Patent: WO2010/65134, 2010, A1, . Location in patent: Page/Page column 60
[5] Journal of the Chemical Society, 1947, p. 808,811
[6] Journal fuer Praktische Chemie (Leipzig), 1929, vol. <2> 120, p. 69
[7] Journal of the American Chemical Society, 1923, vol. 45, p. 1028
[8] Chemistry of Heterocyclic Compounds, 2006, vol. 42, # 1, p. 64 - 69
[9] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 10, p. 5803 - 5814
[10] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8332 - 8338
[11] Organic and Biomolecular Chemistry, 2015, vol. 13, # 47, p. 11486 - 11491
[12] Patent: CN105503668, 2016, A, . Location in patent: Paragraph 0021; 0023
[13] Advanced Synthesis and Catalysis, 2018, vol. 360, # 10, p. 1919 - 1925
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YieldReaction ConditionsOperation in experiment
93% at 0 - 20℃; Inert atmosphere First, into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed methanol/DCM (150/100 mL), 2-amino-4-chlorobenzoic acid (10 g, 58.28 mmol, 1.00 equiv). This was followed by the addition of TMSCHN2 (30.7 mL, 1.05 equiv) dropwise with stirring at 0° C. The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The resulting mixture was washed with 1×20 mL of n-hexane. This resulted in 10.1 g (93percent) of methyl 2-amino-4-chlorobenzoate as a yellow solid.
Reference: [1] Patent: US2015/366198, 2015, A1, . Location in patent: Paragraph 0146
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  • [ 77-76-9 ]
  • [ 89-77-0 ]
  • [ 5900-58-3 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 13, p. 3017 - 3035
[2] Tetrahedron Letters, 2001, vol. 42, # 45, p. 8029 - 8033
  • 40
  • [ 89-77-0 ]
  • [ 5900-58-3 ]
Reference: [1] Patent: US3949081, 1976, A,
[2] Patent: US3989689, 1976, A,
  • 41
  • [ 186581-53-3 ]
  • [ 89-77-0 ]
  • [ 5900-58-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 738 - 743
  • 42
  • [ 67-56-1 ]
  • [ 6341-92-0 ]
  • [ 5900-58-3 ]
  • [ 89-77-0 ]
Reference: [1] Angewandte Chemie, 1981, vol. 93, # 10, p. 914 - 915
  • 43
  • [ 89-77-0 ]
  • [ 5900-59-4 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2 h;
Stage #2: at 0 - 20℃; for 1 h;
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 25percent 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, 88percentyield) as gray solid. 1H NMR (400 MHz, DMSO‑d6) δ: 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) δ: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%
Stage #1: With benzotriazol-1-ol In N,N-dimethyl-formamide for 0.166667 h;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2 h;
Stage #3: With ammonium hydroxide In N,N-dimethyl-formamide at 0 - 20℃; for 2 h;
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 (28percent, 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 (87.6percent 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): δ 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%
Stage #1: With benzotriazol-1-ol In N,N-dimethyl-formamide for 0.166667 h;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2 h;
Stage #3: With ammonium hydroxide In N,N-dimethyl-formamide at 0 - 20℃; for 2 h;
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 (28percent, 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 87.6percent).
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 96 h; [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 10-50percent EtOAc/hexanes to afford 2-amino-4-chlorobenzamide as a solid (2.91 g, 660Zo)-1H NMR (300 MHz, DMSO-J6) δ 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, # 8, p. 198 - 213
[6] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 31, p. 6883 - 6889
[7] Biochemistry, 2017, vol. 56, # 49, p. 6491 - 6502
  • 44
  • [ 89-77-0 ]
  • [ 5900-59-4 ]
YieldReaction ConditionsOperation in experiment
66% With DIEA; benzotriazol-1-ol In N,N-dimethyl-formamide 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 NH3/MeOH (18 mL, 36 mmol), and the solution was stirred at room temperature for 4 days.
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*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 10-50percent EtOAc/hexanes to afford 2-amino-4-chlorobenzamide as a solid (2.91 g, 66percent).
1H NMR (300 MHz, DMSO-d6) 86.50 (dd, J=8.48, 2.26 Hz, 1H), 6.75 (d, J=2.26 Hz, 1H), 6.84 (br s, 2H), 7.18 (br s, 1 H), 7.48-7.63 (m, 1H), 7.80 (br s, 1H).
Reference: [1] Patent: US2012/53176, 2012, A1,
  • 45
  • [ 89-77-0 ]
  • [ 1499-21-4 ]
  • [ 5900-59-4 ]
YieldReaction ConditionsOperation 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,
  • 46
  • [ 89-77-0 ]
  • [ 13421-13-1 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 4, p. 737 - 745
[2] Journal of the American Chemical Society, [3] Journal of the American Chemical Society, 2009, vol. 131, p. 251 - 262
[4] Patent: US2003/187014, 2003, A1,
[5] Collection of Czechoslovak Chemical Communications, 1968, vol. 33, # 6, p. 1852 - 1872
[6] Organic and Biomolecular Chemistry, 2014, vol. 12, # 27, p. 5031 - 5037
[7] Patent: WO2014/189370, 2014, A1, . Location in patent: Page/Page column 27
  • 47
  • [ 89-77-0 ]
  • [ 936-08-3 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 4, p. 737 - 745
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 22, p. 5367 - 5380
  • 48
  • [ 89-77-0 ]
  • [ 59236-37-2 ]
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 18, p. 5530 - 5535
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[3] Patent: WO2013/188724, 2013, A1,
[4] Patent: WO2014/176636, 2014, A1,
[5] Patent: WO2016/112088, 2016, A1,
[6] Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 8966 - 8970
  • 49
  • [ 89-77-0 ]
  • [ 37585-16-3 ]
YieldReaction ConditionsOperation in experiment
88% With borane-THF In tetrahydrofuran at 0 - 30℃; for 1.66667 h; Inert atmosphere General procedure: To a solution of 6-chloroanthranilic acid (1.5 g, 8.74 mmol) in THF (5 mL) was added dropwise 1.08 M borane–tetrahydrofuran complex in THF (24.3 mL, 26.2 mmol) at 0 °C under an Ar atmosphere for 10 min. After 1.5 h with stirring at 30 °C, the solution was cooled at 0 °C, added aqueous THF (THF/H2O = 1:1, 60 mL) and potassium carbonate, and extracted with diethyl ether three times. The combined organic extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was crystallized from AcOEt to give 1a (1.2 g, 88percent) as a white needle crystal.
85.4% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2 h; Inert atmosphere To a mixture of L1AIH4 (4.4 g, 116.6 mmol) in dry THF (116 mL) at 0°C under N2 was added dropwise a solution of 2-amino-4-chlorobenzoic acid (10 g, 58.3 mmol) in dry THF (80 mL). The mixture was stirred at r.t. for 2 hr, then quenched, in sequence, by addition of H2O (4 mL), aq. NaOH (15 wt, 8 mL), and H2O (12 mL). The resulting mixture was filtered, and the filtrate was extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SC>4 and concentrated under reduced pressure. The residue was re -crystallized from EtOAc/PE to give (2-amino-4-chlorophenyl)methanol (7.8 g, 85.4percent yield). LC-MS: m/z 158(M+H)+.
81.6% With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 8 h; Inert atmosphere In a 500 niL round bottom flask, the stirred solution of 2-amino-4-chlorobenzoic acid (42.8 g, 250.29 mmol, Aldrich) was dissolved anhydrous THF (200 mL) and the solution was cooled in an ice-bath. Lithium aluminum hydride (11.76 g, 312.86 mmol) was added portionwise to the above solution at the ice-bath temperature under nitrogen atmosphere. The resulting mixture was stirred at rt for 8 h. On completion of reaction the reaction mixture was cooled to ice-bath temperature and quenched by sequential addition of cold water (12 mL), 15percent NaOH (12 mL) and water (36 mL). The resulting slurry was stirred at rt for 30 min and filtered through a CELITE™ pad. The solid residue was washed with ethyl acetate (1000 mL) and combined filtrate was concentrated under reduced pressure to give (2-amino 4-chlorophenyl)methanol as an off white solid. Yield: 32g (81.6 percent). LCMS (ESI, m/z): 181 (M+23)+.
Reference: [1] ACS Catalysis, 2013, vol. 3, # 4, p. 622 - 624
[2] Chemical Communications, 2017, vol. 53, # 1, p. 216 - 219
[3] Organic Letters, 2017, vol. 19, # 12, p. 3219 - 3222
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[5] Patent: WO2016/112088, 2016, A1, . Location in patent: Paragraph 0214
[6] Patent: WO2013/188724, 2013, A1, . Location in patent: Paragraph 00128
[7] Synlett, 1997, vol. 1997, # 6, p. 704 - 706
[8] Chemistry - A European Journal, 2012, vol. 18, # 18, p. 5530 - 5535
[9] Tetrahedron, 2014, vol. 70, # 34, p. 5114 - 5121
[10] Tetrahedron, 2014, vol. 70, # 34, p. 5114 - 5121
[11] Synthesis (Germany), 2014, vol. 46, # 24, p. 3365 - 3373
[12] Angewandte Chemie, International Edition, 2014, vol. 53, # 36, p. 9603 - 9607,5[13] Angewandte Chemie, 2014, vol. 126, # 36, p. 9757 - 9761,5
[14] Organic Letters, 2015, vol. 17, # 19, p. 4750 - 4753
[15] Organic Letters, 2018,
[16] Patent: JP2015/212297, 2015, A, . Location in patent: Paragraph 0150; 0151
[17] Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 8966 - 8970
[18] Tetrahedron Letters, 2017, vol. 58, # 45, p. 4264 - 4268
  • 50
  • [ 89-77-0 ]
  • [ 37585-16-3 ]
Reference: [1] Patent: US4164407, 1979, A,
  • 51
  • [ 89-77-0 ]
  • [ 50419-88-0 ]
YieldReaction ConditionsOperation in experiment
98% With N-Bromosuccinimide In acetonitrile at 20℃; for 1 h; To 500mL single-necked round-bottomed flask was added4-Chloro-2-aminobenzoic acid(I; 20.00 g, 116.6 mmol),Then acetonitrile (300 mL) was added,Quickly stir,Was a beige suspension,N-bromosuccinimide (NBS; 20.75g, 116.6mmol) was slowly added slowly and slowly at room temperature for several times. After the addition, the reaction was further stirred for 1h, then the solvent was removed by rotary evaporation under a water bath at 45 ° C,Add water and stir,Suction filtration,Washed,At 60 under vacuum drying,The desired target 5-bromo-4-chloro-2-aminobenzoic acid was obtained(II, 28.62 g, 98percent yield).
92% With bromine In methanol at -15 - -10℃; for 2 h; To 2000mLIn a three-necked flask was added methanol (1000 mL, 24.71 mol)4-chloro-2-aminobenzoic acid (20.0 g, 0.11 mol, 1 eq) was added under stirring,After stirring for 5 minutes, the solution was clear,Cooled to -15 ° C with an ice-salt bath,Then bromine (20.6 g, 0.12 mol, 1.1 eq)Was dissolved in methanol (100 mL, 2.47 mol)Slowly drip to the above solution, the reaction exotherm, Dropping speed to keep the internal temperature does not exceed -10 ,After completion of the dropwise addition, the mixture was stirred at -10 ° C for 2 hours,Slowly poured into saturated aqueous sodium thiosulfate solution, and constantly stirring,A large number of white solid precipitation, filter, filter cake washed three times, dry,Dried in vacuo to give the crude product which was recrystallized from methylene chloride,To give 27.0 g of a white solid,Bromo-4-chloro-2-aminobenzoic acid (yield 92percent, HPLC purity 95percent)
62% With bromine In methanol at -78℃; for 2 h; To a solution of 2-amino-4-chlorobenzoic acid (10.0 g, 58.5 mmol) in methanol (150 mL) was added bromine (15.7 mL) at −78° C., and the reaction mixture was stirred at −78° C. for 2 hours. The reaction mixture was quenched with ice water (100 mL) and aq. sodium thiosulfate, and extracted with ethyl acetate (150 mL×3). The organic layers were separated, combined, washed with water (100 mL) and brine (100 mL), dried over sodium sulfate, filtered and concentrated to afford the title compound (9 g, 62percent).
Reference: [1] Patent: CN106986809, 2017, A, . Location in patent: Paragraph 0024; 0025; 0026; 0027; 0028; 0029; 0030
[2] Patent: CN106966914, 2017, A, . Location in patent: Paragraph 0019; 0020; 0028; 0029; 0036; 0037
[3] Patent: US2015/119405, 2015, A1, . Location in patent: Paragraph 0407; 0408; 0409
[4] Patent: WO2005/54238, 2005, A1, . Location in patent: Page/Page column 70
[5] Organic and Biomolecular Chemistry, 2014, vol. 12, # 27, p. 5031 - 5037
[6] Patent: WO2014/189370, 2014, A1, . Location in patent: Page/Page column 27
  • 52
  • [ 89-77-0 ]
  • [ 39061-72-8 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 232,236
[2] Patent: US2011/144115, 2011, A1,
[3] Patent: US2012/129864, 2012, A1,
  • 53
  • [ 89-77-0 ]
  • [ 55496-69-0 ]
Reference: [1] Patent: CN103382182, 2016, B,
[2] Patent: US2009/111772, 2009, A1,
  • 54
  • [ 89-77-0 ]
  • [ 85392-01-4 ]
Reference: [1] Patent: CN105503668, 2016, A,
[2] Patent: CN106243046, 2016, A,
  • 55
  • [ 89-77-0 ]
  • [ 208465-21-8 ]
Reference: [1] Patent: CN106243046, 2016, A,
  • 56
  • [ 89-77-0 ]
  • [ 179552-73-9 ]
Reference: [1] Patent: CN103570738, 2016, B,
  • 57
  • [ 89-77-0 ]
  • [ 179552-75-1 ]
Reference: [1] Patent: US2009/111772, 2009, A1,
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