Methylamine → HCID 69296294, compound

HRID 1930488Notes

Reaction equation

HRID 1930488 reaction equation
[CH:1]1([C:6]2[CH:10]=[C:9]([NH:11][C:12]([NH:14][C:15]3[CH:20]=[C:19]([C:21]4[C:32](=[O:33])[N:31]([CH3:34])[C:24]5[N:25]=[C:26](SC)[N:27]=[CH:28][C:23]=5[CH:22]=4)[CH:18]=[CH:17][C:16]=3[F:35])=[O:13])[N:8]([CH3:36])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:37][NH2:38]>>[CH:1]1([C:6]2[CH:10]=[C:9]([NH:11][C:12]([NH:14][C:15]3[CH:20]=[C:19]([C:21]4[C:32](=[O:33])[N:31]([CH3:34])[C:24]5[N:25]=[C:26]([NH:38][CH3:37])[N:27]=[CH:28][C:23]=5[CH:22]=4)[CH:18]=[CH:17][C:16]=3[F:35])=[O:13])[N:8]([CH3:36])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 69296244HCID 69296244, compound

Product 1

HCID 69296294HCID 69296294, compoundYield 20%

Procedure

Using a procedure analogous to Example A1, 1-(3-cyclopentyl-1-methyl-1H-pyrazol-5-yl)-3-(2-fluoro-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (0.068 g, 0.134 mmol) and MeNH2 (2.0 M in THF, 1.4 mL) were combined to afford 1-(3-cyclopentyl-1-methyl-1H-pyrazol-5-yl)-3-(2-fluoro-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (0.013 g, 20%) as white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.02 (s, 1H), 8.89 (d, J=2.0 Hz, 1H), 8.73 (s, 1H), 8.49 (d, J=7.6 Hz, 1H), 7.95 (m, 1H), 7.92 (m, 1H), 7.38-7.34 (m, 2H), 6.11 (s, 1H), 3.70-3.68 (m, 6H), 2.99-2.94 (m, 4H), 1.99-1.94 (m, 2H), 1.73-1.68 (m, 2H), 1.67-1.60 (m, 4H); MS (ESI) m/z: 491.2 (M+H+).

Sources & evidence

ORD record
ord-03fd30ba7d0446f2bcb4fc5e4e90e456
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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