Acetyl chloride → HCID 178487290, compound

HRID 538081Notes

Reaction equation

HRID 538081 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]2[N:7]([CH3:26])[C:8](=[O:25])[N:9]([CH2:10][C@H:11]3[CH2:16][CH2:15][C@H:14]([C:17]([N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[O:18])[CH2:13][CH2:12]3)[C:5]=2[CH:4]=1.C(N(CC)CC)C.[C:36](Cl)(=[O:38])[CH3:37]>C(Cl)Cl>[C:36]([N:22]1[CH2:21][CH2:20][N:19]([C:17]([C@H:14]2[CH2:15][CH2:16][C@H:11]([CH2:10][N:9]3[C:5]4[CH:4]=[C:3]([O:2][CH3:1])[CH:28]=[CH:27][C:6]=4[N:7]([CH3:26])[C:8]3=[O:25])[CH2:12][CH2:13]2)=[O:18])[CH2:24][CH2:23]1)(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178487289HCID 178487289, compound

Product 1

HCID 178487290HCID 178487290, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Methoxy-1-methyl-3-[trans-4-(piperazine-1-carbonyl)-cyclohexylmethyl]-1,3-dihydro-benzoimidazol-2-one (85 mg, 0.22 mmol) was dissolved in anhydrous DCM (4 ml). Triethyl amine (0.12 ml, 0.66 mmol) and acetyl chloride (0.02 ml, 0.26 mmol) were added and the mixture was stirred at room temperature overnight. The solution was washed with saturated NaHCO3 the organic phase was concentrated and the crude product purified on silica column using EtOAc as eluent to give the titled compound (60 mg, 64%).

Workup

  1. washThe solution was washed with saturated NaHCO3 the organic phase
  2. concentrationwas concentrated
  3. customthe crude product purified on silica column

Sources & evidence

ORD record
ord-f3d6eaa8d3db4c4f800aee9626192a18
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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