HCID 86630626, compound → HCID 68615607, compound

HRID 643720Notes

Reaction equation

HRID 643720 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH2:17][C:18]([NH:21]C=O)([CH3:20])[CH3:19])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:3][CH2:2]1>Cl.CO>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH2:17][C:18]([CH3:19])([NH2:21])[CH3:20])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 86630626HCID 86630626, compound

Product 1

HCID 68615607HCID 68615607, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of N-(2-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}-1,1-dimethylethyl)formamide (Step F, 330 mg, 0.814 mmol) in Hydrogen Chloride, Methanol Reagent 10 (TCI Co.: 4 mL) was stirred at room temperature for 18 h. The reaction mixture was concentrated and the residue was extracted with dichloromethane (30 mL×3). The combined organic layer was washed with saturated sodium hydrogen carbonate aqueous solution (20 mL). The resulting solution was dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=15:1 as eluent) to afford the title compound (199 mg, 65%) as a white amorphous.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe residue was extracted with dichloromethane (30 mL×3)
  3. washThe combined organic layer was washed with saturated sodium hydrogen carbonate aqueous solution (20 mL)
  4. dry with materialThe resulting solution was dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=15:1 as eluent)

Sources & evidence

ORD record
ord-d44eef5d727a4a719fcb6d373de9649f
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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