Methylamine → HCID 69297522, compound

HRID 1930459Notes

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)[CH:21]=[CH:20][C:19]=2[F:38])=[O:16])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:39][NH2:40].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:40][CH3:39])[N:30]=[CH:31][C:26]=4[CH:25]=3)[CH:21]=[CH:20][C:19]=2[F:38])=[O:16])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 6329Methylamine

HCID 8028Tetrahydrofuran

HCID 690355771-(1-tert-butyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(2-fluoro-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea

Product 1

HCID 69297522HCID 69297522, compoundYield 63%

Procedure

Using a procedure analogous to Example A1, 1-(1-tert-butyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(2-fluoro-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (247 mg, 0.449 mmol) and 2.0N methylamine in THF (2.25 mL, 4.49 mmol) were combined to afford 1-(1-tert-butyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(2-fluoro-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (152 mg, 63% yield). 1H NMR (300 MHz, acetone-d6) δ 1.64 (s, 9H), 2.82 (s, 3H), 3.06 (m, 3H), 6.80-6.95 (m, 1H), 7.14-7.19 (m, 1H), 7.38-7.42 (m, 1H), 7.85 (s, 1H), 8.06 (s, 1H), 8.11 (br. s, 1H), 8.50 (br. s, 1H), 8.57-8.59 (m, 1H), 8.60-8.63 (m, 1H); MS (ESI) m/z: 533.3 (M+H+).

Sources & evidence

ORD record: ord-7d000f1eba864dfd8f16a1d3ab82067f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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