Acetic Anhydride → HCID 18668540, compound

HRID 1059243Notes

Reaction equation

HRID 1059243 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([C:19]3[N:20]=[CH:21][N:22]([C:24]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:23]=3)([OH:18])[CH:15]([CH3:17])[CH3:16])=[CH:10][CH:9]=2)[CH:3]=1.[C:43](OC(=O)C)(=[O:45])[CH3:44].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C1COCC1>[OH:18][C:14]([C:11]1[CH:10]=[CH:9][C:8]([C:4]2[CH:3]=[C:2]([NH:1][C:43](=[O:45])[CH3:44])[CH:7]=[CH:6][N:5]=2)=[CH:13][CH:12]=1)([C:19]1[N:20]=[CH:21][N:22]([C:24]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:23]=1)[CH:15]([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 186685231-[4-(4-amino-2-pyridyl)phenyl]-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol

Product 1

HCID 18668540HCID 18668540, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-[4-(4-amino-2-pyridyl)phenyl]-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (1.40 g), acetic anhydride (0.46 ml), triethylamine (0.71 ml) and p-dimethylaminopyridine (20 mg) was stirred in THF (20 ml) at 60° C. for 16 h. The solvent was evaporated and ethyl acetate and water were added to the residue for partitioning. The organic layer was washed with aqueous sodium hydrogen carbonate and brine, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was dissolved in a mixture of acetonitrile (10 ml)—water (10 ml) and tetrabutylammonium bromide (13 mg) was added. The mixture was stirred at room temperature for 10 h. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The organic layer was combined, and the mixture was dried (magnesium sulfate) and concentrated under reduced pressure. The residue was purified by silica gel chomatography (eluent; hexane:ethyl acetate=2:1). Recrystallization from ethyl acetate gave the title compound (630 mg) as colorless powder crystals.

Workup

  1. customThe solvent was evaporated
  2. additionethyl acetate and water were added to the residue
  3. customfor partitioning
  4. washThe organic layer was washed with aqueous sodium hydrogen carbonate and brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in a mixture of acetonitrile (10 ml)—water (10 ml) and tetrabutylammonium bromide (13 mg)
  8. additionwas added
  9. customThe organic layer was separated
  10. extractionthe aqueous layer was extracted with ethyl acetate
  11. dry with materialthe mixture was dried (magnesium sulfate)
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by silica gel chomatography (eluent; hexane:ethyl acetate=2:1)
  14. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-cc5de9a94c1f42b884cc6a1f94252e14
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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