2-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide → 2{4-[4-Chloro-2-(5-chloro-pyridin-2-ylcarbamoyl)-phenylcarbamoyl]-phenyl}-2-methyl-propionic acid methyl ester

HRID 971165Notes

Reaction equation

HRID 971165 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13](Cl)=[O:14])=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[NH2:17][C:18]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:19]=1[C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=1)=[O:21]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:16])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:14])[NH:17][C:18]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:19]=2[C:20](=[O:21])[NH:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 219064182-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamideHCID 251112122-(4-Chlorocarbonylphenyl)-2-methylpropionic acid methyl ester

Product 1

HCID 590197632{4-[4-Chloro-2-(5-chloro-pyridin-2-ylcarbamoyl)-phenylcarbamoyl]-phenyl}-2-methyl-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(4-chlorocarbonyl-phenyl)-2-methyl-propionic acid methyl ester (240.0 mg, 1.0 mmol) in CH2Cl2 at 0° C. was added TEA (3.0 mmol) followed by addition of 2-amino-5-chloro-N-(5-chloro-pyridin-2-yl)-benzamide (281 mg, 1.0 mmol) and DMAP (cat. 10 mg). The resulted mixture was stirred at 0° C. for 1 hr and rt over night. Solvent was evaporated and HPLC purification gave 2{4-[4-Chloro-2-(5-chloro-pyridin-2-ylcarbamoyl)-phenylcarbamoyl]-phenyl}-2-methyl-propionic acid methyl ester as white solid. MS found: (M+1)+=486.2.

Workup

  1. customSolvent was evaporated
  2. customHPLC purification

Sources & evidence

ORD record
ord-07e634630c69496cb24d574e49211709
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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