Ammonia → HCID 11201740, compound

HRID 1831929Notes

Reaction equation

HRID 1831929 reaction equation
[Br:1][C:2]1[C:3](=[O:29])[N:4]([CH2:18][C:19]2[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=2)[C:22](OC)=[O:23])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].[NH3:30]>CO>[Br:1][C:2]1[C:3](=[O:29])[N:4]([CH2:18][C:19]2[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=2)[C:22]([NH2:30])=[O:23])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 11784526HCID 11784526, compound

Product 1

HCID 11201740HCID 11201740, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

A sealed tube containing a solution of methyl 3-[3-bromo-4-(2,4-difluorobenzyloxy)-2-oxo-2H-pyridin-1-ylmethyl]benzoate (0.1 g, 0.21 mmol) and NH3 (3 mL of a 7 N solution in MeOH, 21 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 a white solid (0.06 g, 64%): mp 198-201° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.02-8.00 (m, 2H), 7.85-7.75 (m, 2H), 7.70-7.60 (m, 1H), 7.45-7.30 (m, 4H), 7.17 (t, J=3 Hz, 1H), 6.60 (d, J=9 Hz, 1H), 5.32 (s, 2H), 5.18 (s, 2H). ES HRMS m/z 449.0295 (M+H C20H16BrF2N2O3 requires 449.0307).

Workup

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

Sources & evidence

ORD record
ord-80033e9124f14f9a93d1ad2aa529270e
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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