Methylamine → HCID 69035515, compound

HRID 1930470Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:20](=[O:21])[N:19]([CH3:22])[C:12]3[N:13]=[C:14](SC)[N:15]=[CH:16][C:11]=3[CH:10]=2)=[CH:4][C:3]=1[NH:23][C:24]([NH:26][C:27]1[N:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:30]=[C:29]([CH:38]([CH3:40])[CH3:39])[CH:28]=1)=[O:25].[CH3:41][NH2:42].C1COCC1>>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:20](=[O:21])[N:19]([CH3:22])[C:12]3[N:13]=[C:14]([NH:42][CH3:41])[N:15]=[CH:16][C:11]=3[CH:10]=2)=[CH:4][C:3]=1[NH:23][C:24]([NH:26][C:27]1[N:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:30]=[C:29]([CH:38]([CH3:40])[CH3:39])[CH:28]=1)=[O:25]

Participants

Reactant 3

HCID 6329Methylamine

HCID 8028Tetrahydrofuran

HCID 69297995HCID 69297995, compound

Product 1

HCID 69035515HCID 69035515, compoundYield 52%

Procedure

Using a procedure analogous to Example A1, 1-(2-fluoro-4-methyl-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(3-isopropyl-1-phenyl-1H-pyrazol-5-yl)urea (0.24, 0.43 mmol) and 2 M methylamine in THF (3 eq) were combined to provide 1-(2-fluoro-4-methyl-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(3-isopropyl-1-phenyl-1H-pyrazol-5-yl)urea as a white solid (0.12 g, 52% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.90 (s, 1H), 8.82 (s, 1H), 8.68-8.60 (m, 1H), 7.92 (d, J=8.8 Hz, 1H), 7.82-7.79 (m, 1H), 7.66 (s, 1H), 7.55-7.47 (m, 4H), 7.43-7.39 (m, 1H), 7.12 (d, J=12.4 Hz, 1H), 6.30 (s, 1H), 3.59-3.52 (m, 3H), 2.91-2.80 (m, 4H), 2.05 (s, 3H), 1.18 (d, J=7.2 Hz, 6H); MS (ESI) m/z: 541.3 (M+H+).

Sources & evidence

ORD record: ord-18cfcda0b417453eab961837d9fda30a
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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