Methylamine tetrahydrofuran → HCID 69296308, compound

HRID 1930466Notes

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[O:31][N:30]=[C:29]([CH:32]([CH3:34])[CH3:33])[CH:28]=1)=[O:25].[CH3:35][NH2:36].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:36][CH3:35])[N:15]=[CH:16][C:11]=3[CH:10]=2)=[CH:4][C:3]=1[NH:23][C:24]([NH:26][C:27]1[O:31][N:30]=[C:29]([CH:32]([CH3:34])[CH3:33])[CH:28]=1)=[O:25]

Participants

Reactant 2

HCID 66615946Methylamine tetrahydrofuran

HCID 69089118HCID 69089118, compound

Product 1

HCID 69296308HCID 69296308, compoundYield 21%

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-isopropylisoxazol-5-yl)urea (0.203 g, 0.421 mmol, 1.00 eq) and 2.00M MeNH2/THF (2.10 ml, 4.21 mmol, 10.00 eq,) 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-isopropylisoxazol-5-yl)urea (41 mg, 21% yield) as a pale yellow powder. 1H NMR (400 MHz, DMSO-d6) δ 10.28 (s, 1H), 8.67 (brs, 1H), 8.60 (s, 1H), 7.88 (d, J=8.0 Hz, 1H), 7.81 (brq, J=4.0 Hz, 1H), 7.67 9s, 1H), 7.17 (d, J=12.8 Hz, 1H), 5.96 (s, 1H), 3.59 (s, 3H), 2.90 (d, J=4.8 Hz, 3H), 2.89 (septet, J=7.2 Hz, 1H), 2.08 (s, 3H), 1.16 (d, J=7.2 Hz, 6H); MS (ESI) m/z: 466.0 (M+H+).

Sources & evidence

ORD record: ord-6bff86aafd90421d868c8fb7e1c384a7
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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