Water → HCID 68671556, compound

HRID 2047410Notes

Reaction equation

HRID 2047410 reaction equation
[N:1]1([C:8]2[CH:9]=[C:10]([C:14]3[N:18]([CH3:19])[C:17]4[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=4[N:15]=3)[CH:11]=[CH:12][CH:13]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33].O>ClCCl>[CH3:31][S:32]([N:4]1[CH2:5][CH2:6][CH2:7][N:1]([C:8]2[CH:9]=[C:10]([C:14]3[N:18]([CH3:19])[C:17]4[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=4[N:15]=3)[CH:11]=[CH:12][CH:13]=2)[CH2:2][CH2:3]1)(=[O:34])=[O:33]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68670157HCID 68670157, compound

Product 1

HCID 68671556HCID 68671556, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-[1,4]Diazepan-1-ylphenyl)-1-methyl-1H-benzoimidazole (0.18 g, 0.46 mmol) and triethylamine (0.32 mL, 2.30 mmol) in dichloromethane (4 mL), was added methanesulfonyl chloride (0.04 mL, 0.55 mmol). After 16 h stirring at room temperature water (1 mL) was added, the organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting crude was purified by flash chromatography (eluent:EtOAc) to obtain 0.10 g (54%) of the title compound.

Workup

  1. additionwas added
  2. dry with materialthe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe resulting crude was purified by flash chromatography (eluent:EtOAc)

Sources & evidence

ORD record
ord-e05a84c672b6437abf9ba319c83d6849
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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