HCID 69097937, compound → HCID 69297903, compound

HRID 1930426Notes

Reaction equation

HRID 1930426 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([F:49])=[C:16]([NH:18][C:19](=[O:48])[NH:20][C:21]4[N:25]([CH2:26][CH2:27][N:28]5[CH2:33][CH2:32][N:31](C(OCC6C=CC=CC=6)=O)[CH2:30][CH2:29]5)[N:24]=[C:23]([C:44]([CH3:47])([CH3:46])[CH3:45])[CH:22]=4)[CH:17]=3)[C:9](=[O:50])[N:8]([CH3:51])[C:6]=2[N:7]=1>CCOC(C)=O.[OH-].[Pd+2].[OH-]>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([F:49])=[C:16]([NH:18][C:19]([NH:20][C:21]4[N:25]([CH2:26][CH2:27][N:28]5[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]5)[N:24]=[C:23]([C:44]([CH3:45])([CH3:46])[CH3:47])[CH:22]=4)=[O:48])[CH:17]=3)[C:9](=[O:50])[N:8]([CH3:51])[C:6]=2[N:7]=1

Participants

4

Reactant 1

HCID 69097937HCID 69097937, compound

Product 1

HCID 69297903HCID 69297903, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 4-(2-(5-(3-(5-(2-amino-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl)ureido)-3-tert-butyl-1H-pyrazol-1-yl)ethyl)piperazine-1-carboxylate (0.11 g, 0.16 mmol) in EtOAc (10 mL) was added palladium hydroxide (10% of 10 mg) and the mixture was stirred under a H2 atmosphere for 18 h at RT. Then the mixture was filtered through a Celite pad, the pad was washed with EtOAc (2×5 ml). The filtrate was concentrated to afford a solid which was purified by chromatography using acetonitrile and water as eluents to afford 1-(5-(2-amino-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl)-3-(3-tert-butyl-1-(2-(piperazin-1-yl)ethyl)-1H-pyrazol-5-yl)urea as the amine hydrochloride salt (62 mg, 70% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.20 (brs, 1H), 9.16 (s, 1H), 8.71 (s, 1H), 8.41-8.39 (m, 1H), 7.91 (s, 1H), 7.31-7.29 (m, 2H), 6.18 (s, 1H), 4.44 (brs, 2H), 3.57 (s, 3H), 3.52-3.39 (m, 8H), 1.23 (s, 9H); MS (ESI) m/z: 562.8 (M+H+).

Workup

  1. filtrationThen the mixture was filtered through a Celite pad
  2. washthe pad was washed with EtOAc (2×5 ml)
  3. concentrationThe filtrate was concentrated
  4. customto afford a solid which
  5. customwas purified by chromatography

Sources & evidence

ORD record
ord-278b790de06e4db89524ac835147ccd6
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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