Methylamine → HCID 69037538, compound

HRID 1930486Notes

Reaction equation

HRID 1930486 reaction equation
[C:1]([N:5]1[C:9]([C:10]([F:13])([F:12])[F:11])=[C:8]([NH:14][C:15]([NH:17][C:18]2[CH:23]=[C:22]([C:24]3[C:35](=[O:36])[N:34]([CH3:37])[C:27]4[N:28]=[C:29](SC)[N:30]=[CH:31][C:26]=4[CH:25]=3)[C:21]([CH3:38])=[CH:20][C:19]=2[F:39])=[O:16])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:51][NH2:52]>C1COCC1>[C:1]([N:5]1[C:9]([C:10]([F:13])([F:12])[F:11])=[C:8]([NH:14][C:15]([NH:17][C:18]2[CH:23]=[C:22]([C:24]3[C:35](=[O:36])[N:34]([CH3:37])[C:27]4[N:28]=[C:29]([NH:52][CH3:51])[N:30]=[CH:31][C:26]=4[CH:25]=3)[C:21]([CH3:38])=[CH:20][C:19]=2[F:39])=[O:16])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 70297m-Chloroperbenzoic acidHCID 69297418HCID 69297418, compound

Product 1

HCID 69037538HCID 69037538, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using a procedure analogous to Example A1, 1-(1-tert-butyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(2-fluoro-4-methyl-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (148 mg, 0.263 mmol), MCPBA (81 mg, 0.328 mmol) and 2.0N methylamine in THF (1.3 mL) were combined to afford 1-(1-tert-butyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(2-fluoro-4-methyl-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (103 mg, 71% yield). 1H NMR (300 MHz, DMSO-d6): δ 1.59 (s, 9H), 2.08 (s, 3H), 2.92 (s, 3H), 3.55-3.62 (m, 3H), 7.25-7.30 (m, 1H), 7.69 (s, 1H), 7.70-7.80 (m, 1H), 7.93 (s, 1H), 7.95-8.05 (m, 1H), 8.51 (s, 1H), 8.20-8.25 (m, 1H), 9.04 (s, 1H); MS (ESI) m/z: 547.2 (M+H+).

Sources & evidence

ORD record
ord-d36f0f9ff64d4b7f9b757a698e8ff5de
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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