[ CAS No. 79025-82-4 ]

Name: 79025-82-4|2-Amino-5-chloro-4-methoxybenzoic acid|97%
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Product Details of [ 79025-82-4 ]

CAS No. :	79025-82-4	MDL No. :	MFCD05665825
Formula :	C₈H₈ClNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VJLREPGGNOEDCE-UHFFFAOYSA-N
M.W :	201.61 g/mol	Pubchem ID :	2786373
Synonyms :

Safety of [ 79025-82-4 ]

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

Application In Synthesis of [ 79025-82-4 ]

* 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 [ 79025-82-4 ]
Downstream synthetic route of [ 79025-82-4 ]

[ 79025-82-4 ] Synthesis Path-Upstream 1~3

1
[ 4294-95-5 ]
[ 79025-82-4 ]

Reference： [1] Patent: CN107814792, 2018, A, . Location in patent: Paragraph 0295; 0296

2
[ 50413-30-4 ]
[ 79025-82-4 ]
[ 79025-26-6 ]

Reference： [1] Patent: US4287341, 1981, A,

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[ 4294-95-5 ]
[ 79025-82-4 ]
[ 1180495-74-2 ]

Reference： [1] MedChemComm, 2014, vol. 5, # 12, p. 1892 - 1898

[ 79025-82-4 ] Synthesis Path-Downstream 1~30

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[ 79025-82-4 ]
6-chloro-7-methoxyquinazoline-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%		B. 6-Chloro-7-methoxyquinazoline-2,4-dione (XVIII) Similarly, 6-chloro-7-methoxyquinazoline-2,4-dione was prepared from <strong>[79025-82-4]5-chloro-4-methoxyanthranilic acid</strong> in 83% yield, M.P. 356-8 C. Analysis, Percent Calcd. for C9 H7 ClN2 O3: C, 47.70; H, 3.11; N, 12.36. Found: C, 47.72; H, 3.44; N, 12.27.

Reference： [1]Patent: US4287341,1981,A

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[ 50413-30-4 ]
[ 79025-82-4 ]
[ 79025-26-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With sulfuryl dichloride;	ii. 5-chloro-4-methoxyanthranilic acid (IXc, R=CH3) Treatment of methyl-4-methoxyanthranilate with sulfuryl chloride as described above afforded methyl-4-methoxy-5-chloroanthranilate, M.P., 197-200 C. in 90% yield. Saponification of methyl-4-methoxy-5-chloro anthranilate yielded 5-chloro-4-methoxyanthranilic acid in 64% yield, M.P., 210-3 C. Analysis, Percent Calc'd for C8 H8 ClNO3; C, 47.66; H, 4.00; N, 6.95 Found: C, 48.00; H, 4.11; N, 6.94.

Reference： [1]Patent: US4287341,1981,A

4
2-(3-amino-4-methylphenyl)-1,1,1,3,3,3-hexafluoro-2-propanol [ No CAS ]
[ 79025-82-4 ]
6-Chloro-7-methoxy-3-{2-methyl-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-2-(3-thienylmethyl)-4(3H)-quinazolinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With triphenyl phosphite; phenylacetic acid;	The procedures were carried out similarly to the method described in the literature (Example 1 on page 271 of International Patent Publication WO2003/106435) using 5-chloro-4-methoxyanthranylic acid (201 mg, 1.0 mmol) synthesized by a method described in the literature (Reference Example I, ii of US4287341), phenylacetic acid (142 mg, 1.0 mmol), triphenylphosphite (0.29 ml, 1.1 mmol) and 2-(3-amino-4-methylphenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (273 mg, 1.0 mmol) synthesized by a method described in the literature [Example 147 (1) on page 260 of International Patent Publication WO2005/023782] to obtain the title desired compound as a colorless solid (344 mg, yield: 61%). 1H-NMR (500MHz, DMSO-d6) : delta 8.89 (1H, br) , 8.06 (1H, s), 7.78 (1H, s), 7.70 (1H, d, J = 8.0 Hz), 7.42 (1H, d, J = 8.0 Hz), 7.34-7.41 (2H, m), 6.70 (1H, s), 6.59 (1H, d, J = 5.0 Hz), 4.05 (3H, s), 3.81 (1H, d, J = 15.0 Hz), 3.76 (1H, d, J = 15.0 Hz), 1.63 (3H, s). ESI (ES+) (m/z) : 563 ([M+H]+), ESI (ES-) (m/z) : 561 ( [M-H] +) .

Reference： [1]Patent: EP1764075,2007,A1 .Location in patent: Page/Page column 81

5
[ 4294-95-5 ]
[ 79025-82-4 ]
[ 1180495-74-2 ]

Reference： [1]MedChemComm,2014,vol. 5,p. 1892 - 1898

6
[ 79025-82-4 ]
[ 2243-83-6 ]
2-(2-naphthamido)-5-chloro-4-methoxybenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20.0℃; for 16.0h;	To a solution of <strong>[79025-82-4]2-amino-5-chloro-4-methoxybenzoic acid</strong> (250 mg, 1.24 mmol) in THF (8 mL) and Et3N (1 mL, 7.2 mmol) was added 2-naphthoyl chloride (236 mg, 1.24 mmol) and the resulting solution stirred at ambient temperature for 16 hrs. The reaction was quenched with addition of IN HCl (10 mL) and stirred for 1 hr. Filtration of the precipitate afforded crude product acid which was purified by trituration from hot EtOAc. LC-MS: 356 (M+H)+.

Reference： [1]Patent: WO2017/192304,2017,A1 .Location in patent: Paragraph 0177

7
[ 4294-95-5 ]
[ 79025-82-4 ]

Yield	Reaction Conditions	Operation in experiment
	With N-chlorophthalimide; In acetonitrile; at 75.0℃; for 1.0h;	Step 1: N-chlorophthalimide (1.1 equivalent) was added to a solution of the compound 31a (1 equivalent) in acetonitrile, and the mixture was refluxed at 75 C for 1 hour, and the reaction was terminated by TLC.The solvent was directly dried to give a crude product 31c, which was directly used for the next reaction.

Reference： [1]Patent: CN107814792,2018,A .Location in patent: Paragraph 0295; 0296

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[ 79025-82-4 ]
2,4,6-trichloro-7-methoxyquinazoline [ No CAS ]

Reference： [1]Patent: CN107814792,2018,A

9
[ 79025-82-4 ]
C₁₃H₁₃Cl₂N₃O₂ [ No CAS ]

Reference： [1]Patent: CN107814792,2018,A

10
[ 79025-82-4 ]
C₂₄H₂₈ClN₅O₃S [ No CAS ]

Reference： [1]Patent: CN107814792,2018,A

11
[ 79025-82-4 ]
C₂₄H₃₂ClN₅O₄ [ No CAS ]

Reference： [1]Patent: CN107814792,2018,A

12
[ 590-28-3 ]
[ 79025-82-4 ]
6-chloro-7-methoxyquinazoline-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 2: Intermediate 31c (1 eq.) was dissolved in a mixed solution of acetic acid / water (2:1), and potassium cyanate (3 eq.) was added and stirred at room temperature overnight.The solvent was then sparged, the crude product was taken up in methanol, and a 10% sodium hydroxide solution was added to weakly basic and refluxed for 5 hours.It was then neutralized with concentrated hydrochloric acid to precipitate a gray solid.The filtered crude product 31d was used directly in the next reaction.

Reference： [1]Patent: CN107814792,2018,A .Location in patent: Paragraph 0297; 0298

13
[ 50413-30-4 ]
[ 79025-82-4 ]

Reference： [1]Patent: WO2019/55528,2019,A1

14
[ 79025-26-6 ]
[ 79025-82-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With water; sodium hydroxide; at 20.0℃;	A mixture of compound 2 (26 g, 167 mmol) in a solution of NaOH (13.4 g, 0.334 mmol) in water (400 mL) was stirred at r.t. overnight, after which time complete reaction was observed by TLC. The reaction was acidified with 2N HCl and filtered, washed with water, and dried to provide the desired product as a white solid (30 g, 90% yield). NMR (400 MHz, DMSO-d6) delta: 7 62 (IH, s), 6.44 (IH, s), 3.80 (3H, s).

Reference： [1]Patent: WO2019/55528,2019,A1 .Location in patent: Paragraph 0080

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[ 79025-82-4 ]
C₈H₅Cl₂NOS [ No CAS ]
6-chloro-3-(2,4-dichloro-5-methoxyphenyl)-2-mercapto-7-methoxyquinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21.5 g	With sodium methylate; In isopropyl alcohol;Reflux;	To a mixture of compound 5 (35 g, 149 mmol) and compound 3 (30 g, 149 mmol) in 2-propanol (500 mL) was added NaOMe (402 mg, 7.4 mmol), and the mixture was stirred overnight at reflux. The reaction was concentrated, and the resulting residue was suspended in DCM (200 mL) and filtered. The filter cake was washed with DCM (50 mL) to obtain the product as a white solid (21.5 g, 34% yield over two steps). NMR (400 MHz, DMSO-d6) delta: 13.21 (1H, s), 7.93 (1H, s), 7.79 (1H, s), 7.43 (1H, s), 7.12 (1H, s), 3.98 (3H, s), 3.82 (3H, s); ESI LC-MS: Rt=1.730 min, 418.8 [M+l]+.

Reference： [1]Patent: WO2019/55528,2019,A1 .Location in patent: Paragraph 0082

16
[ 79025-82-4 ]
C₉H₈ClNO₂S [ No CAS ]
6-chloro-3-(2-chloro-4,5-dimethoxyphenyl)-2-mercapto-7-methoxyquinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60 mg	With sodium methylate; isopropyl alcohol;Reflux;	To a mixture of compound 1.5 (323 mg, 1.6 mmol) and compound 1.8 (367 mg, 1.6 mmol) in 2-propanol (6 mL) was added NaOMe (4 mg, 0.08 mmol) and stirred at reflux overnight. The mixture was concentrated and the resulting residue was suspended in DCM (20 ml) and filtered. The filter cake was washed with DCM (5 mL) to afford the product 1 as a white solid (60 mg, 10% yield). ESI/LC-MS: Rt=1.948 min, 413.1[M+1]+. NMR (400 MHz, DMSO) d 13.08 (s, 1H), 7.91 (s, 1H), 7.15 (s, 1H), 7.10 (s, 1H), 7.08 (s, 1H), 3.97 (s, 3H), 3.84 (s, 3H), 3.71 (s, 3H).

Reference： [1]Patent: WO2020/176652,2020,A1 .Location in patent: Paragraph 0082; 0088

17
[ 79025-82-4 ]
C₈H₅ClFNOS [ No CAS ]
6-chloro-3-(2-chloro-4-fluoro-5-methoxyphenyl)-2-mercapto-7-methoxyquinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; isopropyl alcohol;Reflux;	To a mixture of compound 2.8 (500 mg, 2.30 mmol) and compound 1.8 (464 mg,2.3 mmol) in 2-propanol (6 mL) was added NaOMe (6 mg, 0.12 mmol) and the solution was stirred at refluxing overnight. Concentrated and the residue was suspended in DCM (20 ml), filtered and the filter cake was washed with DCM (5 mL) to afford product 2 as white solid (120 mg, 13% yield). ESI LC-MS: Rt=l.656 min, 401.0[M+1]+. NMR (400 MHz, DMSO) 5 13.18 (s, 1H), 7.93 (s, 1H), 7.64 (d, 7= 11.0 Hz, 1H), 7.44 (d, 7= 8.6 Hz, 1H), 7.10 (s, 1H), 3.98 (s, 3H), 3.82 (s, 3H).

Reference： [1]Patent: WO2020/176652,2020,A1 .Location in patent: Paragraph 0089; 0095

18
[ 79025-82-4 ]
[ 306935-82-0 ]
6-chloro-3-(4-chloro-2,5-dimethoxyphenyl)-2-mercapto-7-methoxyquinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56 mg	With sodium methylate; In isopropyl alcohol;Reflux;	To a mixture of compound 3.2 (294 mg, 1.28 mmol) and compound 1.8 (300 mg, 1.28 mmol) in 2-propanol (5 mL) was added NaOMe (4 mg, 0.1 mmol) and the solution was stirred at refluxing overnight. The solvent was removed in vacuo. The residue was purified by Prep-HPLC to provide compound 3 (56 mg, 2% yield). ESI LC-MS: Rt=1.704 min,413.0[M+1]+. NMR (400 MHz, DMSO) d 13.05 (s, 1H), 7.89 (s, 1H), 7.29 (s, 1H), 7.17(s, 1H), 7.08 (s, 1H), 3.95 (s, 3H), 3.75 (s, 3H), 3.69 (s, 3H).

Reference： [1]Patent: WO2020/176652,2020,A1 .Location in patent: Paragraph 0096; 0097

19
[ 79025-82-4 ]
C₇H₂Cl₂FNS [ No CAS ]
6-chloro-3-(2,4-dichloro-5-fluorophenyl)-2-mercapto-7-methoxyquinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
130 mg	With sodium methylate; isopropyl alcohol;Reflux;	To a mixture of compound 4.2 (617 mg, 2.78 mmol) and compound 1.8 (560 mg, 2.78 mmol) in 2-propanol (10 mL) was added NaOMe (8 mg, 0.14 mmol) and the solution was stirred at refluxing overnight. Concentrated and the residue was suspended in DCM (10 ml), filtered and the filter cake was washed with DCM (5 mL) to afford the product 4 as white solid (130 mg, 11% yield ). ESI LC-MS: Rt=l.929 min, 402.8[M-1] . NMR (400 MHz, DMSO) d 13.28 (s, 1H), 8.07 (d, J= 7.2 Hz, 1H), 7.94 (s, 1H), 7.81 (d, J= 9.4 Hz, 1H), 7.10 (s, 1H), 3.98 (s, 3H).

Reference： [1]Patent: WO2020/176652,2020,A1 .Location in patent: Paragraph 0098; 0099

20
[ 79025-82-4 ]
[ 530-62-1 ]
6-chloro-7-methoxy-2H-3,1-benzoxazin-2,4(1H)-dione [ No CAS ]