HCID 69299470, compound → HCID 69297994, compound

HRID 1930449Notes

Reaction equation

HRID 1930449 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]>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][CH2:29][CH2:23][N:30]([CH3:33])[CH3:31])[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

3

Reactant 1

HCID 69299470HCID 69299470, compound

Product 1

HCID 69297994HCID 69297994, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 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 (0.075 g, 0.15 mmol) in THF (1 mL) was added, N1-dimethylethane-1,2-diamine (0.04 g, 0.44 mmol) and stirring continued for 4 h at RT. Solvent was removed under vacuum and crude product was purified by silica gel chromatography to provide 1-(1-tert-butyl-1H-pyrazol-4-yl)-3-(5-(2-(2-(dimethylamino)ethylamino)-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-2-fluoro-4-methylphenyl)urea as the hydrochloride salt (0.058, 74% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.61 (brs, 1H), 8.67-8.64 (m, 2H), 8.42 (s, 1H), 7.95-7.88 (m, 2H), 7.71 (s, 1H), 7.68 (s, 1H), 7.32 (s, 1H), 7.07 (d, J=12.4 Hz, 1H), 3.68-3.65 (m, 2H), 3.57 (s, 3H), 3.28-3.26 (m, 2H), 2.79 (s, 3H), 2.78 (s, 3H), 2.00 (s, 3H), 1.40 (s, 9H); MS (ESI) m/z: 536.2 (M+H+).

Workup

  1. customSolvent was removed under vacuum and crude product
  2. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-527849cff18d4314be73f5d8251bb3a8
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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