Toluene → HCID 57404622, compound

HRID 925597Notes

Reaction equation

HRID 925597 reaction equation
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[CH:17]=[C:18]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[N:19]=[C:20](S(C)(=O)=O)[C:15]4=[N:14][CH:13]=3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[NH2:32][CH2:33][CH2:34][C:35]#[C:36][CH2:37][NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42].C1(C)C=CC=CC=1>CN(C)C=O>[CH:1]1([NH:4][C:5]([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[CH:17]=[C:18]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[N:19]=[C:20]([NH:32][CH2:33][CH2:34][C:35]#[C:36][CH2:37][NH:38][C:39](=[O:45])[O:40][C:41]([CH3:43])([CH3:42])[CH3:44])[C:15]4=[N:14][CH:13]=3)=[CH:8][CH:7]=2)=[O:31])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 53389929HCID 53389929, compoundHCID 86698555HCID 86698555, compound

Product 1

HCID 57404622HCID 57404622, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 75 mg (173 μmol) N-cyclopropyl-4-[8-(methylsulfonyl)-6-phenylimidazo[1,2-a]pyrazin-3-yl]benzamide which was prepared according to intermediate example 9-1 in 0.3 mL N,N-dimethylformamide were added 60 μL tert-butyl (5-aminopent-2-yn-1-yl)carbamate and the mixture was stirred at 50° C. overnight. Toluene was added and the mixture was evaporated. The residue was purified by chromatography to give 23.6 mg (25%) of the title compound

Workup

  1. customthe mixture was evaporated
  2. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-72822390cb034f57b134798fc2ba3106
Source dataset
uspto-grants-2016_03
Patent number
US09284317B2

Reaction notes

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