Water → HCID 71117345, compound

HRID 2368536Notes

Reaction equation

HRID 2368536 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][NH:8][C:9]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[C:30]([F:31])=[CH:29][CH:28]=[C:27]([F:32])[C:26]=3[F:33])=[N:13][CH:12]=2)=[O:10])[C:4]([CH3:34])=[N:3]1.[H-].[Na+].I[CH2:38][CH3:39].O>CN(C=O)C>[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][N:8]([CH2:38][CH3:39])[C:9]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[C:30]([F:31])=[CH:29][CH:28]=[C:27]([F:32])[C:26]=3[F:33])=[N:13][CH:12]=2)=[O:10])[C:4]([CH3:34])=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 71117781HCID 71117781, compound

Product 1

HCID 71117345HCID 71117345, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-((1,3-dimethyl-1H-pyrazol-4-yl)methyl)-1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxamide (508) (70 mg, 0.143 mmol) in DMF (1.5 mL) was added sodium hydride (60% in mineral oil, 7 mg, 0.172 mmol) and the reaction was stirred for 15 minutes. Iodoethane (13 mL, 0.172 mmol) was added and stirred for 1 hour. Water was added slowly and the reaction was extracted with 1:1 EtOAc:Hexane, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (90-100% EtOAc in hexanes) to afford N-((1,3-dimethyl-1H-pyrazol-4-yl)methyl)-N-ethyl-1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxamide (519). 1H NMR (400 MHz, CDCl3) δ: 7.33 (s, 1H), 7.18-6.91 (m, 6H), 6.82-6.73 (m, 1H), 4.37 (s, 2H), 4.34 (s, 2H), 3.77 (s, 3H), 3.37 (q, J=7.0, 2H), 2.16-2.06 (m, 3H), 1.25-1.00 (m, 3H). LC-MS ESI m/z; found 518.0 [M+H]+.

Workup

  1. stirringstirred for 1 hour
  2. extractionthe reaction was extracted with 1:1 EtOAc
  3. dry with materialHexane, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (90-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2642ea80288d46878ae51a5a969aa6cc
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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