Methylamine → HCID 69096056, compound

HRID 1930487Notes

Reaction equation

HRID 1930487 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]([Cl: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]([Cl: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 69042301HCID 69042301, compound

Product 1

HCID 69096056HCID 69096056, compoundYield 62%

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-(4-chloro-2-fluoro-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (80 mg, 0.151 mmol), MCPBA (47 mg, 0.189 mmol) and 2.0N methylamine in THF (0.8 mL) were combined to afford 1-(1-tert-butyl-5-methyl-1H-pyrazol-4-yl)-3-(4-chloro-2-fluoro-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (48 mg, 62% yield). 1H NMR (300 MHz, DMSO-d6): δ 1.49 (s, 9H), 2.27 (s, 3H), 2.89 (s, 3H), 3.49-3.56 (m, 3H), 7.39 (s, 1H), 7.49 (d, 1H), 7.74 (s, 1H), 7.94 (br. s, 1H), 8.17 (d, 1H), 8.29 (s, 1H), 8.62-8.74 (m, 2H); MS (ESI) m/z: 513.0 (M+H+).

Sources & evidence

ORD record
ord-fa63aad51d6a431baf94241088926f5e
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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