Benzenesulfonyl chloride → {4-[(1-Benzenesulfonyl-1H-benzoimidazol-2-ylmethyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester

HRID 1592431Notes

Reaction equation

HRID 1592431 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:21][C:22]1[NH:26][C:25]2[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=2[N:23]=1)[CH2:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[C:39]1([S:45](Cl)(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:21][C:22]1[N:26]([S:45]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=[O:47])=[O:46])[C:25]2[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=2[N:23]=1)[CH2:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 67271501{4-[(1H-benzoimidazol-2-ylmethyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester

Product 1

HCID 67272219{4-[(1-Benzenesulfonyl-1H-benzoimidazol-2-ylmethyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl esterYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of {4-[(1H-benzoimidazol-2-ylmethyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester (0.215 g, 0.51 mmol) in CH2Cl2 (10 mL) was added Et3N (0.30 mL, 2.15 mmol) followed by benzenesulfonyl chloride (0.13 ml, 1.02 mmol) and the resultant solution was stirred at room temperature overnight. The mixture was diluted with CH2Cl2 (40 mL), washed with brine (3×10 mL), dried (Na2SO4), and concentrated. Purification of the crude material by column chromatography on silica gel (15:1 CH2Cl2-MeOH) provided 0.202 g (70%) of {4-[(1-Benzenesulfonyl-1H-benzoimidazol-2-ylmethyl)-(3-methyl-pyridin−2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester as an orange-brown oil.

Workup

  1. washwashed with brine (3×10 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification of the crude material by column chromatography on silica gel (15:1 CH2Cl2-MeOH)

Sources & evidence

ORD record
ord-6386276a3acc40d5be3edf4ac4ff90b6
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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