Methylamine → HCID 69298891, compound

HRID 1930468Notes

Reaction equation

[C:1]([C: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]([CH:33]([CH3:35])[CH3:34])[C:23]4[N:24]=[C:25](SC)[N:26]=[CH:27][C:22]=4[CH:21]=3)[C:17]([CH3:36])=[CH:16][C:15]=2[F:37])=[O:12])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:38][NH2:39]>>[C:1]([C: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]([CH:33]([CH3:35])[CH3:34])[C:23]4[N:24]=[C:25]([NH:39][CH3:38])[N:26]=[CH:27][C:22]=4[CH:21]=3)[C:17]([CH3:36])=[CH:16][C:15]=2[F:37])=[O:12])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 6329Methylamine

HCID 69298828HCID 69298828, compound

Product 1

HCID 69298891HCID 69298891, compoundYield 50%

Procedure

In a procedure analogous to Example A1, 1-(3-tert-butylisoxazol-5-yl)-3-(2-fluoro-5-(8-isopropyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-4-methylphenyl)urea (0.1 g, 0.2 mmol) and methylamine were combined to provide 1-(3-tert-butylisoxazol-5-yl)-3-(2-fluoro-5-(8-isopropyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-4-methylphenyl)urea (45 mg, 50% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.78 (brs, 1H), 8.57 (brs, 1H), 7.85 (d, J=9 Hz, 1H), 7.75 (brs, 1H), 7.62 (s, 1H), 7.15 (d, J=12 Hz, 1H), 6.00 (s, 1H), 5.74 (m, 1H), 2.89 (d, J=5 Hz, 3H), 2.07 (s, 3H), 1.56 (d, J=6 Hz, 6H), 1.21 (s, 9H); MS (ESI) m/z: 508.3 (M+H+).

Sources & evidence

ORD record: ord-16a4da261f1a413dacbbeac46ee04ecc
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

Loading…