Methylamine → HCID 69297474, compound

HRID 1930485Notes

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]([Cl: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]([Cl:38])=[CH:20][C:19]=2[F:39])=[O:16])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 6329Methylamine

HCID 8028Tetrahydrofuran

HCID 70297m-Chloroperbenzoic acid

HCID 69297578HCID 69297578, compound

Product 1

HCID 69297474HCID 69297474, compoundYield 56%

Procedure

Using a procedure analogous to Example A1, 1-(1-tert-butyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(4-chloro-2-fluoro-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (230 mg, 0.394 mmol), MCPBA (126 mg, 0.512 mmol) and 2.0N methylamine in THF (1.97 mL, 3.94 mmol) were combined to afford 1-(1-tert-butyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(4-chloro-2-fluoro-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (127 mg, 56% yield). 1H NMR (300 MHz, DMSO-d6), δ 1.59 (s, 9H), 2.92 (s, 3H), 3.53-3.62 (m, 3H), 7.55-7.65 (m, 1H), 7.78 (s, 1H), 7.80-7.90 (m, 1H), 7.93 (s, 1H), 8.15-8.25 (m, 1H), 8.45-8.70 (m, 2H), 9.25 (s, 1H); MS (ESI) m/z: 567.0 (M+H+).

Sources & evidence

ORD record: ord-ea17044fc1624d16ad6371ab8312cf07
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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