HCID 57406685, compound → HCID 57404623, compound

HRID 925599Notes

Reaction equation

HRID 925599 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([NH:28][CH2:29][CH:30]([CH3:32])[CH3:31])[C:10]3[N:11]([C:13]([C:16]4[CH:27]=[CH:26][C:19]([C:20]([NH:22][CH:23]5[CH2:25][CH2:24]5)=[O:21])=[CH:18][CH:17]=4)=[CH:14][N:15]=3)[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>C(O)C.[Pd]>[CH:1]1([C:7]2[N:8]=[C:9]([NH:28][CH2:29][CH:30]([CH3:32])[CH3:31])[C:10]3[N:11]([C:13]([C:16]4[CH:27]=[CH:26][C:19]([C:20]([NH:22][CH:23]5[CH2:24][CH2:25]5)=[O:21])=[CH:18][CH:17]=4)=[CH:14][N:15]=3)[CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 57406685HCID 57406685, compound

Product 1

HCID 57404623HCID 57404623, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 52 mg (0.12 mmol) 4-{6-(cyclohex-1-en-1-yl)-8-[(2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl}-N-cyclopropylbenzamide (example 1-3) in 8 mL ethanol was added 5 mg 10% Pd/C and the mixture was stirred at rt and normal pressure overnight under hydrogen atmosphere. The mixture was filtered and purified by HPLC to yield 20.8 mg (40%) of the title compound. UPLC-MS: RT=1.39 min; m/z (ES+) 432.6 [MH+]; required MW=431.6. 1H-NMR (CDCl3): δ=0.65 (2H), 0.89 (2H), 1.02 (6H), 1.17-1.54 (5H), 1.67-2.07 (6H), 2.42 (1H), 2.94 (1H), 3.47 (2H), 6.06 (1H), 6.39 (1H), 7.34 (1H), 7.53 (1H), 7.59 (2H), 7.89 (2H) ppm.

Workup

  1. customnormal pressure overnight
  2. filtrationThe mixture was filtered
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-ee6efe7abdc14ef7a1c83387cbe59943
Source dataset
uspto-grants-2016_03
Patent number
US09284317B2

Reaction notes

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