Cyclopropylamine → HCID 69299514, compound

HRID 1930461Notes

Reaction equation

HRID 1930461 reaction equation
[C:1]([N:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[C:31](=[O:32])[N:30]([CH3:33])[C:23]4[N:24]=[C:25]([NH:28][CH3:29])[N:26]=[CH:27][C:22]=4[CH:21]=3)[C:17]([CH3:34])=[CH:16][C:15]=2[F:35])=[O:12])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH:36]1(N)C[CH2:37]1>C1COCC1>[C:1]([N:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[C:31](=[O:32])[N:30]([CH3:33])[C:23]4[N:24]=[C:25]([NH:28][CH:29]5[CH2:37][CH2:36]5)[N:26]=[CH:27][C:22]=4[CH:21]=3)[C:17]([CH3:34])=[CH:16][C:15]=2[F:35])=[O:12])[CH:7]=[N:6]1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 69299470HCID 69299470, compound

Product 1

HCID 69299514HCID 69299514, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using general method E, 1-(1-tert-butyl-1H-pyrazol-4-yl)-3-(2-fluoro-4-methyl-5-(8-methyl-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea from Example 109 (0.081 g, 0.16 mmol) and cyclopropanamine (0.027 g, 0.48 mmol) were combined in THF (1 mL) to provide 1-(1-tert-butyl-1H-pyrazol-4-yl)-3-(5-(2-(cyclopropylamino)-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-2-fluoro-4-methylphenyl)urea as a white solid (0.051 g, 64% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.64 (s, 1H), 8.60 (brs, 1H), 8.40 (d, J=1.6 Hz, 1H), 8.06-8.04 (m, 1H), 7.94 (d, J=8.8 Hz, 1H), 7.77 (s, 1H), 7.66 (s, 1H), 7.36 (s, 1H), 7.10 (d, J=12.4 Hz, 1H), 3.61-3.54 (m, 3H), 2.78-2.83 (m, 1H), 2.05 (s, 3H), 1.45 (s, 9H), 0.725 (brs, 2H), 0.55-0.53 (m, 2H); (ESI) m/z: 505.2 (M+H+).

Sources & evidence

ORD record
ord-18f981cbc4354afb8ae3bcaf89d76f49
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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