Methylamine → HCID 69036549, compound

HRID 1930464Notes

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

Participants

Reactant 2

HCID 6329Methylamine

HCID 69298815HCID 69298815, compound

Product 1

HCID 69036549HCID 69036549, compoundYield 50%

Procedure

Using a procedure analogous to Example A1, 1-(3-tert-butylisoxazol-5-yl)-3-(4-chloro-2-fluoro-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea and methylamine were combined to provide 1-(3-tert-butylisoxazol-5-yl)-3-(4-chloro-2-fluoro-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (88 mg, 50% yield). 1H NMR (400 MHz, DMSO-d6): δ10.5 (brs, 1H), 9.00 (brs, 1H), 8.61 (s, 1H), 8.11 (d, J=9 Hz, 1H), 7.88 (brs, 1H), 7.76 (s, 1H), 7.57 (d, J=12 Hz, 1H), 6.00 (s, 1H), 3.58 (s, 3H), 2.89 (d, J=5 Hz, 3H), 1.21 (s, 9H); MS (ESI) m/z: 500.3 (M+H+).

Sources & evidence

ORD record: ord-bc4ffaf79ad44042b2961ec8de75d314
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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