Sodium hydride → HCID 10182998, compound

HRID 1644858Notes

Reaction equation

HRID 1644858 reaction equation
[H-].[Na+].[N:3]1([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:19]=[C:18]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:17][C:16]=3[C:24]([NH2:26])=[O:25])=[CH:11][CH:10]=2)[CH:7]=[CH:6][N:5]=[CH:4]1.[CH2:27]([S:31](Cl)(=[O:33])=[O:32])[CH2:28][CH2:29][CH3:30]>C1COCC1>[CH2:27]([S:31]([NH:26][C:24]([C:16]1[S:17][C:18]([CH2:20][CH:21]([CH3:22])[CH3:23])=[CH:19][C:15]=1[C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:3]2[CH:7]=[CH:6][N:5]=[CH:4]2)=[CH:10][CH:11]=1)=[O:25])(=[O:33])=[O:32])[CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 754301-Butanesulfonyl chlorideHCID 11645798HCID 11645798, compound

Product 1

HCID 10182998HCID 10182998, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

NaH (55%, 12 mg, 0.28 mmol) was added to a solution of 3-(4-imindazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-carboxamide (46 mg, 0.136 mmol, see step (e) above) in THF (1 mL). The mixture was stirred at 50° C. for 0.5 hours. Butanesulfonyl chloride (29 μL, 0.223 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 1 hour. The mixture was concentrated and purified using silica gel chromatography (CH2Cl2:MeOH, 9:1) to give 31 mg of the title compound as a white powder (yield: 50%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 1 hour
  2. concentrationThe mixture was concentrated
  3. custompurified

Sources & evidence

ORD record
ord-82917549fd0c4b4da31f75757320346d
Source dataset
uspto-grants-2012_02
Patent number
US08124638B2

Reaction notes

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