Methylamine → HCID 69040265, compound

HRID 1930445Notes

Reaction equation

HRID 1930445 reaction equation
[C:1]([N: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]([CH:33]([CH3:35])[CH3:34])[C:23]4[N:24]=[C:25](SC)[N:26]=[CH:27][C:22]=4[CH:21]=3)[CH:17]=[CH:16][C:15]=2[F:36])=[O:12])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:37][NH2:38]>C1COCC1>[C:1]([N: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]([CH:33]([CH3:35])[CH3:34])[C:23]4[N:24]=[C:25]([NH:38][CH3:37])[N:26]=[CH:27][C:22]=4[CH:21]=3)[CH:17]=[CH:16][C:15]=2[F:36])=[O:12])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 69296298HCID 69296298, compound

Product 1

HCID 69040265HCID 69040265, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using a procedure analogous to Example A1, 1-(1-tert-butyl-1H-pyrazol-4-yl)-3-(2-fluoro-5-(8-isopropyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (0.065 g, 0.13 mmol) and 2 M methylamine in THF (1 mL) were combined to afford 1-(1-tert-butyl-1H-pyrazol-4-yl)-3-(2-fluoro-5-(8-isopropyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea as white solid (39 mg, 62%). 1H NMR (400 MHz, DMSO-d6): δ 8.68 (s, 1H), 8.62 (s, 1H), 8.48 (d, J=2.0 Hz, 1H), 8.34 (d, J=7.6 Hz, 1H), 7.80 (s, 1H), 7.79 (s, 1H), 7.78-7.74 (m, 1H), 7.38 (s, 1H), 7.22-7.20 (m, 2H), 5.77-5.74 (m, 1H), 2.89 (d, J=4.4 Hz, 3H), 1.59-1.55 (m, 6H), 1.46 (m, 9H); MS (ESI) m/z: 493.2 (M+H+).

Sources & evidence

ORD record
ord-00c0c853947c4dbc9d24918b15ad7f44
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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