Methylamine → HCID 69299470, compound

HRID 1930447Notes

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)[C:17]([CH3:34])=[CH:16][C:15]=2[F:35])=[O:12])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:36][NH2:37].C1COCC1>>[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:37][CH3:36])[N:26]=[CH:27][C:22]=4[CH:21]=3)[C:17]([CH3:34])=[CH:16][C:15]=2[F:35])=[O:12])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 6329Methylamine

HCID 8028Tetrahydrofuran

HCID 69036851HCID 69036851, compound

Product 1

HCID 69299470HCID 69299470, compoundYield 94%

Procedure

Using a procedure analogous to Example A1, 1-(1-tert-butyl-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 (0.192 g, 0.39 mmol) and 2M methylamine in THF (1 mL; 5 eq) were combined to afford 1-(1-tert-butyl-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 as an off-white solid (0.174 g, 94% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.63 (s, 1H), 8.60 (s, 1H), 8.40 (d, J=1.6 Hz, 1H), 7.94 (d, J=8.8 Hz, 1H), 7.80-7.77 (m, 2H), 7.66 (s, 1H), 7.36 (s, 1H), 7.10 (d, J=8.4 Hz, 1H), 3.59-3.51 (m, 3H), 2.90 (d, J=4.4 Hz, 1H), 2.05 (s, 3H), 1.45 (s, 9H); (ESI) m/z: 479.2 (M+H+).

Sources & evidence

ORD record: ord-b902e55ec183431d97cd004ac2a63804
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

Loading…