Methylamine → HCID 86270234, compound

HRID 1472619Notes

Reaction equation

HRID 1472619 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)[C:5]([F:21])=[CH:4][C:3]=1[NH:22][C:23]([C:25]1[C:26](=[O:39])[N:27]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH:28]=[CH:29][C:30]=1I)=[O:24].[CH3:40][NH2:41]>>[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)[C:5]([F:21])=[CH:4][C:3]=1[NH:22][C:23]([C:25]1[C:26](=[O:39])[N:27]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH:28]=[CH:29][C:30]=1[NH:41][CH3:40])=[O:24]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 90447769HCID 90447769, compound

Product 1

HCID 86270234HCID 86270234, compoundYield 36%

Procedure

A mixture of Example A5 (100 mg, 0.155 mmol) in a methanolic solution of MeNH2 (10 mL) was heated at 80° C. for 3 h. The mixture was concentrated to dryness and purified by HPLC to afford N-(2,5-difluoro-4-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)phenyl)-1-(4-fluorophenyl)-4-(methylamino)-2-oxo-1,2-dihydropyridine-3-carboxamide (31 mg, 36%). 1H-NMR (400 MHz, CD3OD): δ 8.64 (br, s, 1H), 8.49 (br, s, 1H), 8.42 (br, s, 1H), 8.13 (br, s, 1H), 7.64 (br, s, 3H), 7.56 (br, s, 2H), 7.37-7.16 (m, 4H), 6.33 (br, s, 1H), 3.98 (s, 3H), 3.09 (s, 3H); MS (ESI) m/z: 547.2 (M+H+).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-c5213e9e73b14e1299823092567c103f
Source dataset
uspto-grants-2015_04
Patent number
US09012635B2

Reaction notes

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