Acetyl chloride → HCID 118093877, compound

HRID 1056967Notes

Reaction equation

HRID 1056967 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]([CH3:18])[C:7](=[O:17])[N:8]([CH2:9][CH2:10][N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:4]=2[C:3]=1[O:21][CH2:22][CH:23]1[CH2:26][CH2:25][CH2:24]1.C(N(CC)C(C)C)(C)C.[C:36](Cl)(=[O:38])[CH3:37]>C(Cl)Cl>[C:36]([N:14]1[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][N:8]2[C:4]3[C:3]([O:21][CH2:22][CH:23]4[CH2:26][CH2:25][CH2:24]4)=[C:2]([Br:1])[CH:20]=[CH:19][C:5]=3[N:6]([CH3:18])[C:7]2=[O:17])[CH2:16][CH2:15]1)(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 118093891HCID 118093891, compound

Product 1

HCID 118093877HCID 118093877, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-bromo-4-(cyclobutylmethoxy)-1-methyl-3-(2-piperazin-1-ylethyl)-1,3-dihydro-2H-benzimidazol-2-one (40.0 mg, 0.0945 mmol) in methylene chloride (2.0 mL) was treated with N,N-diisopropylethylamine (49.4 μL, 0.283 mmol) followed by the addition of acetyl chloride (10.1 μL, 0.142 mmol), and the resultant reaction mixture was stirred at RT for 1 h. Purification by flash column chromatography (5% MeOH/EtOAc) gave the desired product (46 mg, 94%). LCMS calculated for C21H30BrN4O3 (M+H)+: m/z=465.1, 467.1. found: 465.1, 467.1.

Workup

  1. customthe resultant reaction mixture
  2. customPurification by flash column chromatography (5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-f4b656daab3e4e7eb19a9704d57f0ab1
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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