N-methyl-2-pyrrolidone → HCID 178432257, compound

HRID 74454Notes

Reaction equation

HRID 74454 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20]([S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:21]2[C:26]([CH:27]=1)=[CH:25][C:24](I)=[CH:23][CH:22]=2)=[O:18].[Cu][C:39]#[N:40].CN1CCCC1=O.O.N>CO.C(OCC)(=O)C>[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20]([S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([C:39]#[N:40])=[CH:23][CH:22]=2)=[O:18]

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 12896473Azane;hydrateHCID 178418546HCID 178418546, compoundHCID 178432261HCID 178432261, compound

Product 1

HCID 178432257HCID 178432257, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-[5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazole-4-carbonyl]-1-(benzenesulfonyl)-5-iodo-1H-indole (117 mg), copper (I) cyanide (84 mg), and 1-methyl-2-pyrrolidinone was reacted in a microwave reactor (190° C., 20 minutes). The reaction mixture was poured into a mixed solution of 2 M ammonia water (40 ml), ethyl acetate (60 ml), and methanol (7 ml), and sonicated for five minutes. After ethyl acetate extraction, the extract was washed with water and then dried over anhydrous sodium sulfate. The desiccant was removed by filtration. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (methanol/dichloromethane=0/100 to 20/100) to give 2-[5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazole-4-carbonyl]-1-(benzenesulfonyl)-1H-indole-5-carbonitrile (87 mg, 89%).

Workup

  1. customwas reacted in a microwave reactor (190° C., 20 minutes)
  2. customsonicated for five minutes
  3. extractionAfter ethyl acetate extraction
  4. washthe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe desiccant was removed by filtration
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (methanol/dichloromethane=0/100 to 20/100)

Sources & evidence

ORD record
ord-7f4a445e6e354b8ca6233dd93c3c46fa
Source dataset
uspto-grants-2014_09
Patent number
US08829199B2

Reaction notes

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