Pyridine → HCID 59426182, compound

HRID 252576Notes

Reaction equation

HRID 252576 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[C:5]([C:16]#[N:17])=[C:4]1[N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH3:2].N1C=CC=CC=1.[CH:30]1([S:33](Cl)(=[O:35])=[O:34])[CH2:32][CH2:31]1>ClCCl>[CH:30]1([S:33]([N:21]2[CH2:20][CH2:19][N:18]([C:4]3[N:3]([CH2:1][CH3:2])[C:11]4[C:6]([C:5]=3[C:16]#[N:17])=[CH:7][CH:8]=[C:9]([C:12]([F:14])([F:15])[F:13])[CH:10]=4)[CH2:23][CH2:22]2)(=[O:35])=[O:34])[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2760919Cyclopropanesulfonyl chlorideHCID 59426299HCID 59426299, compound

Product 1

HCID 59426182HCID 59426182, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-ethyl-2-piperazin-1-yl-6-(trifluoromethyl)-1H-indole-3-carbonitrile (32 mg, 0.1 mmol), pyridine (0.1 mL) in dichloromethaene (1.0 mL) is added cyclopropanesulfonyl chloride (28 mg, 0.2 mmol) and the mixture is stirred at room temperature overnight. This is then diluted with dichloromethane (5 mL), washed with HCl (2 N, 2×2 mL), water (2×5 mL) and brine (5 mL) and chromatographed over silica gel (dichloromethane/ethyl acetate, 9/1) to provide 2-[4-(cyclopropylsulfonyl)piperazin-1-yl]-1-ethyl-6-(trifluoromethyl)-1H-indole-3-carbonitrile, compound 842 (30 mg, 70%).

Workup

  1. washwashed with HCl (2 N, 2×2 mL), water (2×5 mL) and brine (5 mL)
  2. customchromatographed over silica gel (dichloromethane/ethyl acetate, 9/1)

Sources & evidence

ORD record
ord-8d52c4802b314e05b336d76a481f0fb2
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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