4-Acetylpiperazine-1-carbothioamide → 1-(4-(4-(2,3-Dichloro-4-(2-isopropyl-phenylsulfanyl)-phenyl)-thiazol-2-yl)-piperazin-1-yl)-ethanone

HRID 1246833Notes

Reaction equation

HRID 1246833 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]([CH3:20])[CH3:19])=[C:7]([Cl:21])[C:6]=1[Cl:22])=O.[C:23]([N:26]1[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH2:27]1)(=[S:25])[NH2:24]>CN(C=O)C>[Cl:22][C:6]1[C:7]([Cl:21])=[C:8]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]([CH3:20])[CH3:19])[CH:9]=[CH:10][C:5]=1[C:3]1[N:24]=[C:23]([N:26]2[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH2:27]2)[S:25][CH:2]=1

Participants

4

Reactant 2

HCID 20505104-Acetylpiperazine-1-carbothioamideHCID 219067782-Bromo-1-(2,3-dichloro-4-(2-isopropyl-phenylsulfanyl)-phenyl)-ethanone

Product 1

HCID 161176841-(4-(4-(2,3-Dichloro-4-(2-isopropyl-phenylsulfanyl)-phenyl)-thiazol-2-yl)-piperazin-1-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of compound 41 (30 mg, 0.07 mmole) and 1-thiocarbamyl-4-acetyl piperazine (20.5 mg, 0.11 mmole) in DMF (1.0 ml) was stirred at ambient temperature for two hours. The solvent was evaporated and the residue was purified on a 5-g silica gel cartridge, giving the desired product 39 as a white solid. 23 mg, 65.7%. 1H-NMR (CDCl3, 500 MHz) δ 1.19 (d, J=8.5 Hz, 6H), 2.14 (s, 3H), 3.46–3.60 (m, 7H),), 3.75–3.78 (m, 2H), 6.48 (d, J=8.4 Hz, 1H), 7.09 (s, 1H), 7.21 (m, 1H), 7.44–7.51 (m, 3H), 7.57 (d, J=8.4 Hz, 1H). MS (DCI/NH3) m/z 506 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified on a 5-g silica gel cartridge

Sources & evidence

ORD record
ord-ae237afb592c43e5b30f9a050037e43b
Source dataset
uspto-grants-2006_10
Patent number
US07129247B2

Reaction notes

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