Ethenesulfonyl chloride, 2-phenyl- → (E)-2-Phenyl-ethenesulfonic acid (1-acetyl-2,3-dihydro-1H-indol-6-yl)-(1-benzyl-piperidin-4-yl)-amide

HRID 2250870Notes

Reaction equation

HRID 2250870 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:23]=[C:22]3[C:18]([CH2:19][CH2:20][N:21]3[C:24](=[O:26])[CH3:25])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]1([CH:33]=[CH:34][S:35](Cl)(=[O:37])=[O:36])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[C:24]([N:21]1[C:22]2[C:18](=[CH:17][CH:16]=[C:15]([N:14]([CH:11]3[CH2:12][CH2:13][N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:9][CH2:10]3)[S:35](/[CH:34]=[CH:33]/[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:37])=[O:36])[CH:23]=2)[CH2:19][CH2:20]1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 107500Ethenesulfonyl chloride, 2-phenyl-HCID 27611281-Acetyl-N-(1-benzylpiperidin-4-yl)-indolin-6-amine

Product 1

HCID 11398198(E)-2-Phenyl-ethenesulfonic acid (1-acetyl-2,3-dihydro-1H-indol-6-yl)-(1-benzyl-piperidin-4-yl)-amideYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[6-(1-benzyl-piperidin-4-ylamino)-2,3-dihydro-indol-1-yl]-ethanone (0.10 g, 0.29 mmol), 2-phenyl-ethenesulfonyl chloride (87 mg, 0.43 mmol), and TEA (0.08 mL, 0.57 mmol) in CH2Cl2 (5 mL) was stirred at rt for 20 h. The reaction mixture was concentrated, and the residue was purified on silica gel (60-70% EtOAc/hexanes) to afford the title compound (138 mg, 92%). 1H NMR (500 MHz, CDCl3): 8.12 (s, 1H), 7.50-7.48 (m, 2H), 7.43 (s, 1H), 7.41-7.39 (m, 3H), 7.25 (d, J=6.8 Hz, 2H), 7.20 (t, J=7.0 Hz, 3H), 7.15 (d, J=7.9 Hz, 1H), 6.91 (d, J=7.8 Hz, 1H), 6.86 (d, J=15.0 Hz, 1H), 4.13 (t, J=8.0 Hz, 2H), 3.98-3.40 (m, 1H), 3.41 (s, 2H), 3.20 (t, J=8.5 Hz, 2H), 2.87 (d, J=10.5 Hz, 2H), 2.20 (s, 3H), 2.06-2.02 (m, 2H), 1.88 (d, J=10.7 Hz, 2H), 1.61-1.55 (m, 2H). MS: exact mass calculated for C30H33N3O3S, 515.22; m/z found, 516.3 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified on silica gel (60-70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-15b5e6189a304b08a968f2b662cbffb6
Source dataset
uspto-grants-2008_01
Patent number
US07317025B2

Reaction notes

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