HCID 71735444, compound → HCID 178439598, compound

HRID 707319Notes

Reaction equation

HRID 707319 reaction equation
[CH3:1][C:2]1([CH3:26])[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH:11]2[CH2:14][CH:13]([NH:15][C:16]3[N:21]=[CH:20][C:19]([C:22]([CH3:24])=[CH2:23])=[CH:18][N:17]=3)[CH2:12]2)[C:3]1=[O:25]>C(O)C.C(OCC)(=O)C.[Pd]>[CH:22]([C:19]1[CH:18]=[N:17][C:16]([NH:15][C@H:13]2[CH2:14][C@H:11]([N:4]3[C:5]4=[N:6][CH:7]=[CH:8][CH:9]=[C:10]4[C:2]([CH3:1])([CH3:26])[C:3]3=[O:25])[CH2:12]2)=[N:21][CH:20]=1)([CH3:24])[CH3:23]

Participants

5

Reactant 1

HCID 71735444HCID 71735444, compound

Product 1

HCID 178439598HCID 178439598, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Palladium (10 wt. % on activated carbon, 3.53 mg, 3.32 μmol) was added to a mixture of 3,3-dimethyl-1-(−3-((5-(prop-1-en-2-yl)pyrimidin-2-yl)amino)cyclobutyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (example 80, 58 mg, 0.166 mmol) in ethanol (1 mL) and ethyl acetate (0.5 mL) under an argon atmosphere. The reaction mixture was placed under a hydrogen atmosphere (balloon) and stirred at room temperature for 6 hours. The reaction mixture was filtered through celite, and the filtrate was concentrated to yield 1-(trans-3-((5-isopropylpyrimidin-2-yl)amino)cyclobutyl)-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one as a yellow solid. M+1: 352.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.19 (d, J=6.85 Hz, 6 H) 1.31 (s, 6 H) 2.23-2.39 (m, 2 H) 2.76 (spt, J=6.94 Hz, 1 H) 3.14-3.26 (m, 2 H) 4.47-4.59 (m, 1 H) 5.16 (quin, J=8.51 Hz, 1 H) 7.08 (dd, J=7.24, 5.28 Hz, 1 H) 7.53 (br. d, J=6.50 Hz, 1 H) 7.76 (dd, J=7.24, 1.57 Hz, 1 H) 8.21 (dd, J=5.28, 1.56 Hz, 1 H) 8.24 (s, 2 H)

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0ee01c84572c46cbaa6732f274d10b05
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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