Methylamine → HCID 69298838, compound

HRID 1930444Notes

Reaction equation

HRID 1930444 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[C:31](=[O:32])[N:30]([CH3:33])[C:23]4[N:24]=[C:25](SC)[N:26]=[CH:27][C:22]=4[CH:21]=3)[C:17]([CH3:34])=[CH:16][C:15]=2[F:35])=[O:12])[N:7]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:53][NH2:54]>C1COCC1>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[C:31](=[O:32])[N:30]([CH3:33])[C:23]4[N:24]=[C:25]([NH:54][CH3:53])[N:26]=[CH:27][C:22]=4[CH:21]=3)[C:17]([CH3:34])=[CH:16][C:15]=2[F:35])=[O:12])[N:7]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 70297m-Chloroperbenzoic acidHCID 69297385HCID 69297385, compound

Product 1

HCID 69298838HCID 69298838, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using a procedure analogous to Example A1, 1-(3-tert-butyl-1-phenyl-1H-pyrazol-5-yl)-3-(2-fluoro-4-methyl-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (0.25, 0.43 mmol), MCPBA (0.081 g, 0.47 mmol) and 2 M methylamine in THF (1 mL) were combined to provide 1-(3-tert-butyl-1-phenyl-1H-pyrazol-5-yl)-3-(2-fluoro-4-methyl-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea as white solid (0.17 g, 72% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.90 (d, J=2.0 Hz, 1H), 8.81 (s, 1H), 8.60 (s, 1H), 7.93 (d, J=8.4 Hz, 1H), 7.83-7.78 (m, 1H), 7.65 (s, 1H), 7.54-7.47 (m, 4H), 7.43-7.38 (m, 1H), 7.11 (d, J=12.0 Hz, 1H), 6.34 (s, 1H), 3.59 (s, 3H), 2.90 (d, J=4.4 Hz, 1H), 2.05 (s, 3H), 1.23 (s, 9H); MS (ESI) m/z; 555.2 (M+H+).

Sources & evidence

ORD record
ord-ba18f6702f6e4bc390d27658ab76c887
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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