Methylamine → HCID 69297876, compound

HRID 1930457Notes

Reaction equation

HRID 1930457 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[C:19](=[O:20])[N:18]([CH3:21])[C:11]3[N:12]=[C:13](SC)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:6][C:5]([NH:22][C:23]([NH:25][C:26]2[O:30][N:29]=[C:28]([C:31]([F:34])([F:33])[F:32])[CH:27]=2)=[O:24])=[C:4]([F:35])[CH:3]=1.[CH3:36][NH2:37]>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]2[C:19](=[O:20])[N:18]([CH3:21])[C:11]3[N:12]=[C:13]([NH:37][CH3:36])[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:6][C:5]([NH:22][C:23]([NH:25][C:26]2[O:30][N:29]=[C:28]([C:31]([F:34])([F:33])[F:32])[CH:27]=2)=[O:24])=[C:4]([F:35])[CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 69297541HCID 69297541, compound

Product 1

HCID 69297876HCID 69297876, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using a procedure analogous to Example A1, 1-(4-chloro-2-fluoro-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(3-(trifluoromethyl)isoxazol-5-yl)urea (75 mg, 0.140 mmol) and 2.0 N methylamine in THF (0.71 mL) were combined to afford 1-(4-chloro-2-fluoro-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(3-(trifluoromethyl)isoxazol-5-yl)urea (15 mg, 21% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.89 (s, 3H), 3.51-3.58 (m, 3H), 6.48 (s, 1H), 7.61 (d, J=11 Hz, 1H), 7.77 (s, 1H), 7.88-7.90 (m, 1H), 8.04 (d, J=9.5 Hz, 1H), 8.61-8.69 (m, 1H), 9.01 (s, 1H), 11.0 (s, 1H); MS (ESI) m/z: 512.0 (M+H+).

Sources & evidence

ORD record
ord-fa1375ad1c344d638b6b24ceea50c067
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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