Methylamine → HCID 71575823, compound

HRID 1411151Notes

Reaction equation

HRID 1411151 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[C:17]([F:18])=[CH:16][C:15]([NH:19][C:20]([C:22]3[C:23](=[O:36])[N:24]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)[CH:25]=[CH:26][C:27]=3I)=[O:21])=[C:14]([F:37])[CH:13]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].[CH3:38][NH2:39]>>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[C:17]([F:18])=[CH:16][C:15]([NH:19][C:20]([C:22]3[C:23](=[O:36])[N:24]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)[CH:25]=[CH:26][C:27]=3[NH:39][CH3:38])=[O:21])=[C:14]([F:37])[CH:13]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 86703363HCID 86703363, compound

Product 1

HCID 71575823HCID 71575823, compoundYield 85.5%

Procedure

A methanolic solution of methylamine (10 mL) was added to 1-(4-fluoro-phenyl)-4-iodo-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid [4-(2-acetylamino-pyridin-4-yloxy)-2,5-difluoro-phenyl]-amide (90 mg, 0.145 mmol) and the resultant mixture was stirred at 80° C. for 3 h. The mixture was concentrated to dryness and the crude product was recrystallized from MeOH to afford N-(4-((2-acetamidopyridin-4-yl)oxy)-2,5-difluorophenyl)-1-(4-fluorophenyl)-4-(methylamino)-2-oxo-1,2-dihydropyridine-3-carboxamide (65 mg, 85.5% yield). 1H NMR (400 MHz, DMSO-d6): δ 13.21 (s, 1H), 10.57 (s, 1H), 10.34 (m, 1H), 8.47 (dd, J=13.0, 7.2 Hz, 1H), 8.17 (d, J=5.8 Hz, 1H), 7.72 (d, J=7.8 Hz, 1H), 7.65 (s, 1H), 7.55-7.42 (m, 3H), 7.33 (m, 2H), 6.69 (d, J=5.9 Hz, 1H), 6.24 (d, J=7.9 Hz, 1H), 3.01 (d, J=5.0 Hz, 3H), 2.02 (s, 3H); MS (ESI) m/z: 524.01 (M+H+).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customthe crude product was recrystallized from MeOH

Sources & evidence

ORD record
ord-72cc298bad274cc7a2e8ae891ed4c097
Source dataset
uspto-grants-2014_12
Patent number
US08921565B2

Reaction notes

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