Pyridine → HCID 57708180, compound

HRID 643722Notes

Reaction equation

HRID 643722 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]([CH3:21])([NH2:20])[CH3:19])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:3][CH2:2]1.N1C=CC=CC=1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>ClCCl>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH2:17][C:18]([NH:20][C:33](=[O:35])[CH3:34])([CH3:19])[CH3:21])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 68615607HCID 68615607, compound

Product 1

HCID 57708180HCID 57708180, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}-2-methylpropan-2-amine (step G, of EXAMPLE 18, 39 mg, 0.1 mmol) in dichloromethane (0.5 mL) were added pyridine (0.016 mL, 0.2 mmol) and acetic anhydride (0.012 mL, 0.12 mmol) at room temperature. After 4 h, the reaction was quenched by addition of water (10 mL) and the organic layer was separated. The aqueous layer was extracted with dichloromethane (10 mL×2) and the combined organic layer was washed with water (10 mL), brine (5 mL) and dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel TLC eluting with hexane/ethyl acetate (1/5) to afford 33 mg (78%) of the title compound.

Workup

  1. customthe reaction was quenched by addition of water (10 mL)
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with dichloromethane (10 mL×2)
  4. washthe combined organic layer was washed with water (10 mL), brine (5 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel TLC
  9. washeluting with hexane/ethyl acetate (1/5)

Sources & evidence

ORD record
ord-c69d584058f44abdab44b259e71bcf1a
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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