Trityl chloride → 1-(cyclopropylmethyl)-2-neopentyl-5-(1-tritylpiperidin-4-ylsulfonyl)-1H-benzo[d]imidazole

HRID 241647Notes

Reaction equation

HRID 241647 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:35]1([C:41](Cl)([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>ClCCl>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH:17]4[CH2:22][CH2:21][N:20]([C:41]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)([C:48]5[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=5)[C:42]5[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=5)[CH2:19][CH2:18]4)(=[O:15])=[O:16])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 585136051-(cyclopropylmethyl)-2-neopentyl-5-(piperidin-4-ylsulfonyl)-1H-benzo[d]imidazole

Product 1

HCID 585135841-(cyclopropylmethyl)-2-neopentyl-5-(1-tritylpiperidin-4-ylsulfonyl)-1H-benzo[d]imidazoleYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(cyclopropylmethyl)-2-neopentyl-5-(piperidin-4-ylsulfonyl)-1H-benzo[d]imidazole (STEP D, 1.31 g, 3.36 mmol) and triethylamine (945 microL, 6.73 mmol) in dichloromethane (12 mL) was added triphenylmethyl chloride (1.22 g, 4.37 mmol) at room temperature. After stirring for 14 h, the mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate aqueous solution. The organic layer was dried over sodium sulfate and concentrated in vacuo. The precipitate was washed with a mixture of diethyl ether and hexane (1:1) to give the title compound (1.99 g, 94%) as a white solid.

Workup

  1. washwashed with saturated sodium bicarbonate aqueous solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. washThe precipitate was washed with a mixture of diethyl ether and hexane (1:1)

Sources & evidence

ORD record
ord-c76b13e4543f432ab08024ad648c8c2b
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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