Carbon Dioxide → Prx-07034

HRID 2426017Notes

Reaction equation

HRID 2426017 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:29][CH3:30])[C:5]([O:27][CH3:28])=[C:6]([CH:8]([NH:10][C:11]2[CH:16]=[C:15]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH:14]=[CH:13][C:12]=2[S:23]([CH3:26])(=[O:25])=[O:24])[CH3:9])[CH:7]=1.C(=O)=O.CO.Cl>ClCCl.CCOCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([O:29][CH3:30])[C:5]([O:27][CH3:28])=[C:6]([CH:8]([NH:10][C:11]2[CH:16]=[C:15]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH:14]=[CH:13][C:12]=2[S:23]([CH3:26])(=[O:24])=[O:25])[CH3:9])[CH:7]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 887MethanolHCID 11532574PRX-07034 free base

Product 1

HCID 23653584Prx-07034Yield 196.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

[1-(5-Chloro-2,3-dimethoxy-phenyl)-ethyl]-(2-methanesulfonyl-5-piperazin-1-yl-phenyl)-amine (10 mg, 0.022 mmol) was dissolved in dichloromethane (1.5 mL) and ether (1.5 mL). The solution was cooled in a bath with dry ice and methanol. Hydrochloric acid (0.5 mL, 2.0 M in ether) was added slowly. The mixture was warmed to room temperature. The solvents were concentrated down in vacuo and co-evaporated with diethyl ether gave [1-(5-chloro-2,3-dimethoxy-phenyl)-ethyl]-(2-methanesulfonyl-5-piperazin-1-yl-phenyl)-amine hydrochloride salt as a white solid (10.6 mg): 1H NMR (400 MHz, CD3OD): 1H NMR (400 MHz, CD3OD): δ 7.51 (d, 1H), 6.92 (m, 2H), 6.37 (dd, 1H), 6.09 (d, 1H), 4.93 (m, 1H), 3.90 (s, 3H), 3.86 (s, 3H), 3.48 (m, 4H), 3.24 (m, 4H), 3.05 (s, 3H), 1.49 (d, 3H). MS (ESI) m/z: Calculated: 453.98 free base; Observed: 454.4 (M+H+); 476.4 (M+Na+); 930.8 (2M+Na+). Salt: Mol. Wt.: 490.44 (C21H29Cl2N3O4S).

Workup

  1. concentrationThe solvents were concentrated down in vacuo and co-evaporated with diethyl ether

Sources & evidence

ORD record
ord-921966cb285448a299e20224224c86c8
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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