Trimethylsilyl isocyanate → 4-[4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-piperidine-1-carboxylic acid amide

HRID 1433089Notes

Reaction equation

HRID 1433089 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[C:15](=[O:26])[CH2:14]3)(=[O:12])=[O:11])[S:7][C:6]=2[CH:27]=1.C[Si]([N:32]=[C:33]=[O:34])(C)C>ClCCCl.C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH:20]4[CH2:21][CH2:22][N:23]([C:33]([NH2:32])=[O:34])[CH2:24][CH2:25]4)[C:15](=[O:26])[CH2:14]3)(=[O:12])=[O:11])[S:7][C:6]=2[CH:27]=1

Participants

5

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 670148114-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-1-piperidin-4-ylmethyl-piperazin-2-one

Product 1

HCID 670150024-[4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-piperidine-1-carboxylic acid amide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-1-piperidin-4-ylmethyl-piperazin-2-one (20 mg, 0.047 mmol) in a mixture of 1,2-dichloroethane (1 mL) and THF (1 mL) is added trimethylsilyl isocyanate (0.006 mL, 0.05 mmol) and stirred 60 hours. The reaction is concentrated and purified by column chromatography (silica, 20% methanol/dichloromethane) to provide 4-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-piperidine-1-carboxylic acid amide. 1H NMR (300 MHz, CD3OD) d 8.09 (s, 1H), 8.02 (d, 2H), 7.53 (dd, 1H), 3.90 (d, 4H), 3.49 (d, 4H), 3.30-3.24 (m, 2H), 2.65 (dt, 2H), 1.49 (d, 2H), 1.12-0.97 (m, 2H); MS (Ion spray) 471 (M+H).

Workup

  1. concentrationThe reaction is concentrated
  2. custompurified by column chromatography (silica, 20% methanol/dichloromethane)

Sources & evidence

ORD record
ord-8ec72476067949eab87d9bc429d26165
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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