Acetic Anhydride → HCID 59083091, compound

HRID 2416923Notes

Reaction equation

HRID 2416923 reaction equation
[CH:1]1([N:7]([CH3:31])[C:8]([C:10]2[CH:30]=[CH:29][C:13]3[N:14]([CH2:25][CH2:26][CH2:27][OH:28])[C:15]([NH:17][C:18]([C:20]4[S:21][CH:22]=[CH:23][CH:24]=4)=[O:19])=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:32](OC(=O)C)(=[O:34])[CH3:33].C(N(CC)CC)C>C1COCC1>[CH:1]1([N:7]([CH3:31])[C:8]([C:10]2[CH:30]=[CH:29][C:13]3[N:14]([CH2:25][CH2:26][CH2:27][O:28][C:32](=[O:34])[CH3:33])[C:15]([NH:17][C:18]([C:20]4[S:21][CH:22]=[CH:23][CH:24]=4)=[O:19])=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 10160476HCID 10160476, compound

Product 1

HCID 59083091HCID 59083091, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3-hydroxy-propyl)-2-[(thiophene-2-carbonyl)-amino]-1H-benzoimidazole-5-carboxylic acid cyclohexyl-methyl-amide (Example 4) (0.07 g, 0.16 mmol) in THF (10 mL) was added acetic anhydride (0.02 mL, 0.19 mmol), followed by triethylamine (0.02 mL, 0.17 mmol), and the mixture was stirred at room temperature for 48 h. The resulting solution was washed with 1M HCl (10 mL) and the organic layer was dried over magnesium sulfate. The solvent was evaporated and the resulting oil was purified by flash chromatography with 5% MeOH/dichloromethane to give the title compound (0.05 g, 65%), m.p. 74-76° C.

Workup

  1. washThe resulting solution was washed with 1M HCl (10 mL)
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe resulting oil was purified by flash chromatography with 5% MeOH/dichloromethane

Sources & evidence

ORD record
ord-ad829218054a4e5d91caa55643152843
Source dataset
uspto-grants-2004_11
Patent number
US06825219B2

Reaction notes

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