Acetyl chloride → HCID 86757198, compound

HRID 1386930Notes

Reaction equation

HRID 1386930 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=3)[CH2:18][N:19]3[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20]3)[N:11]=2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:35]([Cl:38])(=[O:37])[CH3:36].Cl.CCO>C(Cl)Cl>[ClH:38].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[NH:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=3)[CH2:18][N:19]3[CH2:23][CH2:22][CH:21]([O:24][C:35](=[O:37])[CH3:36])[CH2:20]3)[N:11]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21180500HCID 21180500, compoundHCID 21887872Ethanol hydrochloride

Product 1

HCID 86757198HCID 86757198, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (RS)-1-{3-[5-(4-methoxy-phenyl)-1H-[1,2,4]triazol-3-yl]-benzyl}-pyrrolidin-3-ol hydrochloride (1:1) (mixture of tautomers) (50 mg, 0.13 mmol) in CH2Cl2 (5 ml) was treated with triethylamine (26 mg, 0.26 mmol 2 eq.) and stirred for 30 min. at r.t. Acetyl chloride (11 mg, 0.13 mmol, 1 eq.) was added and stirring was continued for 1.5 hrs. After removal of the solvent the residue was chromatographed over 20 g SiO2 (Merck 230-400 mesh) with CH2Cl2-MeOH (2M NH3) 96:4. The resulting product was dissolved in ethanol at r.t. and an excess 1.45 N HCl/EtOH solution (0.1 ml, 0.14 mmol) was added. After 30 min. stirring the solvent was evaporated and the residue dried under high vacuum at 40° C. overnight affording the title compound (53 mg, 0.12 mmol, 96% yield) as a colorless solid. MS: m/e=393.2 (M+H+)

Workup

  1. stirringstirring
  2. waitwas continued for 1.5 hrs
  3. customAfter removal of the solvent the residue
  4. customwas chromatographed over 20 g SiO2 (Merck 230-400 mesh) with CH2Cl2-MeOH (2M NH3) 96:4
  5. dissolutionThe resulting product was dissolved in ethanol at r.t.
  6. stirringAfter 30 min. stirring the solvent
  7. customwas evaporated
  8. customthe residue dried under high vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-ffcc3675e90a4f30916fd7a58c48874f
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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