Iodoacetamide → HCID 24960550, compound

HRID 244406Notes

Reaction equation

HRID 244406 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[NH:10][CH:11]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[N:21]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[N:20]=[CH:19]3)[C:12]([F:15])([F:14])[F:13])[CH:3]=[CH:2]1.[OH-].[K+].I[CH2:35][C:36]([NH2:38])=[O:37]>CN(C=O)C>[F:14][C:12]([F:15])([F:13])[CH:11]([NH:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[N:1]([CH2:35][C:36]([NH2:38])=[O:37])[CH:2]=[CH:3]2)[C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[N:20]=[CH:19]2

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 14797Potassium HydroxideHCID 59437266HCID 59437266, compound

Product 1

HCID 24960550HCID 24960550, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a chilled (0° C.) solution of 78 mg (0.18 mmol) of (1H-Indol-7-yl)-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}amine in 5 mL of DMF was added 15 mg (1.09 mmol) of powder KOH followed by 37 mg (1.09 mmol) of iodoacetamide. The mixture stirred overnight at room temperature. The mixture was then poured onto ice water and extracted with three 20 mL portions of ethyl acetate. The combined organic layers were washed with brine, saturated aqueous ammonium chloride, brine, and dried over sodium sulfate. The crude material was loaded onto a silica cartridge and purified by Combiflash chromatography using a 0-60% EtOAc-hexanes (0-60% gradient) to afford 30 mg (38%) of the title compound as a colorless foam, m.p. 105° C.

Workup

  1. additionThe mixture was then poured onto ice water
  2. extractionextracted with three 20 mL portions of ethyl acetate
  3. washThe combined organic layers were washed with brine, saturated aqueous ammonium chloride, brine
  4. dry with materialdried over sodium sulfate
  5. custompurified by Combiflash chromatography

Sources & evidence

ORD record
ord-57bd557f25bb45368092e8a15028d892
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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