Triethylamine → 2-(5-Bromo-2-((tert-butoxycarbonylamino)methyl)-1H-benzo[d]imidazol-1-yl)ethyl methanesulfonate

HRID 882060Notes

Reaction equation

HRID 882060 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([CH2:18][CH2:19][OH:20])[C:7]([CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[N:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[CH3:30][S:31]([O:20][CH2:19][CH2:18][N:6]1[C:5]2[CH:21]=[CH:22][C:2]([Br:1])=[CH:3][C:4]=2[N:8]=[C:7]1[CH2:9][NH:10][C:11]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:17])(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57514768tert-Butyl ((5-bromo-1-(2-hydroxyethyl)-1H-benzo[d]imidazol-2-yl)methyl)carbamate

Product 1

HCID 575147692-(5-Bromo-2-((tert-butoxycarbonylamino)methyl)-1H-benzo[d]imidazol-1-yl)ethyl methanesulfonateYield 106.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl ((5-bromo-1-(2-hydroxyethyl)-1H-benzo[d]imidazol-2-yl)methyl)carbamate (648 mg, 1.75 mmol) was stirred in methylene chloride (25 mL), and triethylamine (530 mg, 0.74 mL, 5.3 mmol) and methanesulfonyl chloride (400 mg, 0.27 mL, 3.5 mmol) were added. The mixture was stirred for 2 h and then washed with water, dried over sodium sulfate and concentrated to provide the title compound (833 mg, quant) as a yellow solid: ESI MS m/z 448 [M+H]+.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9b5a01ebf3874948994fdb779f3c237b
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

Loading…