Methylamine → HCID 69296291, compound

HRID 1930465Notes

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]([CH2:33][CH3:34])[C:23]4[N:24]=[C:25](SC)[N:26]=[CH:27][C:22]=4[CH:21]=3)[C:17]([CH3:35])=[CH:16][C:15]=2[F:36])=[O:12])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:37][NH2:38]>>[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]([CH2:33][CH3:34])[C:23]4[N:24]=[C:25]([NH:38][CH3:37])[N:26]=[CH:27][C:22]=4[CH:21]=3)[C:17]([CH3:35])=[CH:16][C:15]=2[F:36])=[O:12])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 6329Methylamine

HCID 69297402HCID 69297402, compound

Product 1

HCID 69296291HCID 69296291, compoundYield 20%

Procedure

Using a procedure analogous to Example A1, 1-(3-tert-butylisoxazol-5-yl)-3-(5-(8-ethyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-2-fluoro-4-methylphenyl)urea (0.16 g, 0.315 mmol) and methylamine were combined to provide 1-(3-tert-butylisoxazol-5-yl)-3-(5-(8-ethyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-2-fluoro-4-methylphenyl)urea (62 mg, 20% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.3 (brs, 1H), 8.67 (brs, 1H), 8.61 (brs, 1H), 7.88 (d, J=9 Hz, 1H), 7.80 (brs, 1H), 7.66 (s, 1H), 7.16 (d, J=12 Hz, 1H), 6.00 (s, 1H), 5.73 (s, 1H), 4.34 (br, 2H), 2.89 (d, J=6 Hz, 3H), 2.07 (s, 3H), 1.21 (br, 12H); MS (ESI) m/z: 494.2 (M+H+).

Sources & evidence

ORD record: ord-5bc2c0ddcfdb4a09adf28fb0e1e12d84
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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