Methylamine tetrahydrofuran → HCID 69298827, compound

HRID 1930460Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:20](=[O:21])[N:19]([CH3:22])[C:12]3[N:13]=[C:14](SC)[N:15]=[CH:16][C:11]=3[CH:10]=2)=[CH:4][C:3]=1[NH:23][C:24]([NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=1)=[O:25].[CH3:37][NH2:38].C1COCC1>>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:20](=[O:21])[N:19]([CH3:22])[C:12]3[N:13]=[C:14]([NH:38][CH3:37])[N:15]=[CH:16][C:11]=3[CH:10]=2)=[CH:4][C:3]=1[NH:23][C:24]([NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=1)=[O:25]

Participants

Reactant 2

HCID 66615946Methylamine tetrahydrofuran

HCID 69297375HCID 69297375, compound

Product 1

HCID 69298827HCID 69298827, compoundYield 31.1%

Procedure

Using a procedure analogous to Example A1, 1-(2-fluoro-4-methyl-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(3-(trifluoromethyl)phenyl)urea (0.092 g, 0.18 mmol) and 2.00M MeNH2/THF (0.89 ml, 1.8 mmol) were combined to afford 1-(2-fluoro-4-methyl-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(3-(trifluoromethyl)phenyl)urea (28 mg, 31% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.78 (s, 1H), 8.61 (s, 1H), 8.12-8.09 (m, 2H), 8.04 (s, 1H), 7.68 s, 1H), 7.64 (brd, J=10.0 Hz, 1H), 7.50 (dd, J=7.6 and 16.0 Hz, 1H), 7.31 (brd, J=7.6 Hz, 1H), 7.06 (d, J=12.4 Hz, 1H), 6.82 (brs, 1H), 3.59 (s, 3H), 3.08 (brd, J=4.4 Hz, 3H), 2.16 (s, 3H); MS (ESI) m/z: 501.0 (M+H+).

Sources & evidence

ORD record: ord-6bbbd5f0c254458a8b868b57b3af3a4e
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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