Methylamine → HCID 69037736, compound

HRID 1930484Notes

Reaction equation

HRID 1930484 reaction equation
[C:1]([N:5]1[C:9]([CH3:10])=[C:8]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[C:19]([C:21]3[C:32](=[O:33])[N:31]([CH3:34])[C:24]4[N:25]=[C:26](SC)[N:27]=[CH:28][C:23]=4[CH:22]=3)[C:18]([CH3:35])=[CH:17][C:16]=2[F:36])=[O:13])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:48][NH2:49]>C1COCC1>[C:1]([N:5]1[C:9]([CH3:10])=[C:8]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[C:19]([C:21]3[C:32](=[O:33])[N:31]([CH3:34])[C:24]4[N:25]=[C:26]([NH:49][CH3:48])[N:27]=[CH:28][C:23]=4[CH:22]=3)[C:18]([CH3:35])=[CH:17][C:16]=2[F:36])=[O:13])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 70297m-Chloroperbenzoic acidHCID 69297542HCID 69297542, compound

Product 1

HCID 69037736HCID 69037736, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using a procedure analogous to Example A1, 1-(1-tert-butyl-5-methyl-1H-pyrazol-4-yl)-3-(2-fluoro-4-methyl-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (31 mg, 0.061 mmol), MCPBA (19 mg, 0.079 mmol) and 2.0N methylamine in THF (0.4 mL) were converted to 1-(1-tert-butyl-5-methyl-1H-pyrazol-4-yl)-3-(2-fluoro-4-methyl-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (15 mg, 50% yield). 1H NMR (300 MHz, DMSO-d6), δ 1.60 (s, 9H), 2.20 (s, 3H), 2.35 (s, 3H), 2.95 (s, 3H), 3.60-3.70 (m, 3H), 7.20-7.25 (m, 1H), 7.50 (s, 1H), 7.70 (s, 1H), 7.70-7.90 (m, 1H), 8.05 (m, 1H), 8.20 (s, 1H), 8.55 (m, 1H), 8.70-8.80 (m, 1H); MS (ESI) m/z: 493.0 (M+H+).

Sources & evidence

ORD record
ord-13f92e6965764b07b2997e2aa31af936
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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