Methylamine tetrahydrofuran → HCID 69297861, compound

HRID 1930473Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:15]=[C:14]([C:23]([F:26])([F:25])[F:24])[CH:13]=2)=[O:10])=[CH:4][C:3]=1[C:27]1[C:38](=[O:39])[N:37]([CH3:40])[C:30]2[N:31]=[C:32](SC)[N:33]=[CH:34][C:29]=2[CH:28]=1.[CH3:41][NH2:42].C1COCC1>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:15]=[C:14]([C:23]([F:26])([F:25])[F:24])[CH:13]=2)=[O:10])=[CH:4][C:3]=1[C:27]1[C:38](=[O:39])[N:37]([CH3:40])[C:30]2[N:31]=[C:32]([NH:42][CH3:41])[N:33]=[CH:34][C:29]=2[CH:28]=1

Participants

Reactant 2

HCID 66615946Methylamine tetrahydrofuran

HCID 69297669HCID 69297669, compound

Product 1

HCID 69297861HCID 69297861, compoundYield 78%

Procedure

Using a procedure analogous to example A1, 1-(4-methyl-3-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)urea (0.1231 g, 0.218 mmol) and 2.0M MeNH2/THF (1.088 ml, 2.177 mmol) were combined to afford 1-(4-methyl-3-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)urea (93 mg, 78% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.08 (s, 1H), 8.69 (s, 1H), 8.59 (s, 1H), 7.81 (brq, J=4.4 Hz, 1H), 7.66 (s, 1H), 7.63-7.52 (m, 5H), 7.30 (d, J=2.0 Hz, 1H) 7.21 (dd, J=2.0 and 8.4 Hz, 1H), 7.13 (d, J=8.4 Hz, 1H), 6.85 (s, 1H), 3.59 (s, 3H), 2.90 (brd, J=4.8 Hz, 3H), 2.05 (s, 3H); MS (ESI) m/z: 549.3 (M+H+).

Sources & evidence

ORD record: ord-192eac32f9404258bfba29bc8057c666
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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