Ammonia → HCID 11165621, compound

HRID 1831920Notes

Reaction equation

HRID 1831920 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[C:13]([Cl:27])[C:12]2=[O:28])=[CH:6][CH:5]=1.[NH3:30]>CO>[Cl:27][C:13]1[C:12](=[O:28])[N:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([NH2:30])=[O:2])=[CH:5][CH:6]=2)[CH:16]=[CH:15][C:14]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[F:26]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22050850HCID 22050850, compound

Product 1

HCID 11165621HCID 11165621, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

A sealed tube containing a solution of 4-[3-Chloro-4-(2,4-difluorobenzyloxy)-2-oxo-2H-pyridin-1-ylmethyl]benzoic acid methyl ester (0.25 g, 0.60 mmol) and NH3 (20 mL of a 7 N solution in MeOH, 140 mmol) was heated at 75° C. for 16 h. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Trituration with Et2O/MeOH afforded 4-[3-Chloro-4-(2,4-difluorobenzyloxy)-2-oxo-2H-pyridin-1-ylmethyl]benzamide as a white solid (0.14 g, 60%): mp 235-238° C.; 1H NMR (500 MHz, DMSO-d6) δ 7.93 (d, J=8 Hz, 2H), 7.79 (d, J=8 Hz, 2H), 7.60 (app q, J=8 Hz, 1H), 7.35-7.27 (m, 4H), 7.20-7.10 (m, 1H), 6.61 (d, J=8 Hz, 1H), 5.28 (s, 2H), 5.14 (s, 2H). ES HRMS m/z 405.0788 (M+H C20H16ClF2N2O3 requires 405.0812)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dddc73be5a8b4588933188ddab910a50
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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