Methylamine → HCID 69297575, compound

HRID 1930434Notes

Reaction equation

[C:1]([N: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)[CH:17]=[CH:16][C:15]=2[F:34])=[O:12])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:35][NH2:36]>>[C:1]([N: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:36][CH3:35])[N:26]=[CH:27][C:22]=4[CH:21]=3)[CH:17]=[CH:16][C:15]=2[F:34])=[O:12])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 6329Methylamine

HCID 69296201HCID 69296201, compound

Product 1

HCID 69297575HCID 69297575, compoundYield 66%

Procedure

Using a procedure analogous to Example A1, 1-(1-tert-butyl-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 (0.3 g, 0.63 mmol) and methyl amine (1.3 ml of 1M solution, 1.3 mmol) were combined to afford 1-(1-tert-butyl-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 as a white solid (0.135 g, 66% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.73-8.70 (m, 1H), 8.65 (s, 1H), 8.48 (d, J=2.0 Hz, 1H), 8.41-8.39 (m, 1H), 7.85 (s, 1H), 7.81 (brs, 2H), 7.38 (s, 1H), 7.24-7.22 (m, 2H), 3.61-3.57 (m, 3H), 2.90 (d, J=4.0 Hz, 1H), 2.60 (s, 3H), 1.46 (s, 9H); (ESI) m/z: 465.2 (M+H*).

Sources & evidence

ORD record: ord-1eaeac67bcd94f57b76d39e56adabe7b
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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