Diisopropylethylamine → 1-[4-(4-Methanesulfonyl-phenoxymethyl)-thiazol-2-yl]-4-(2-methyl-propane-1-sulfonyl)-piperazine

HRID 871933Notes

Reaction equation

HRID 871933 reaction equation
Cl.[CH3:2][S:3]([C:6]1[CH:24]=[CH:23][C:9]([O:10][CH2:11][C:12]2[N:13]=[C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[S:15][CH:16]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4].CCN(C(C)C)C(C)C.[CH2:34]([S:38](Cl)(=[O:40])=[O:39])[CH:35]([CH3:37])[CH3:36]>C(Cl)Cl>[CH3:2][S:3]([C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][C:12]2[N:13]=[C:14]([N:17]3[CH2:22][CH2:21][N:20]([S:38]([CH2:34][CH:35]([CH3:37])[CH3:36])(=[O:40])=[O:39])[CH2:19][CH2:18]3)[S:15][CH:16]=2)=[CH:23][CH:24]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1822361-Propanesulfonyl chloride, 2-methyl-HCID 669109741-[4-(4-Methanesulfonyl-phenoxymethyl)-thiazol-2-yl]-piperazine hydrochloride

Product 1

HCID 579868251-[4-(4-Methanesulfonyl-phenoxymethyl)-thiazol-2-yl]-4-(2-methyl-propane-1-sulfonyl)-piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-[4-(4-Methanesulfonyl-phenoxymethyl)-thiazol-2-yl]-piperazine hydrochloride (100 mg, 0.26 mmol) and DIPEA (134 mL, 3 eq.) in CH2Cl2 (5 mL) was added isobutanesulfonyl chloride (41 mL, 1.2 eq.). The mixture was stirred for 1 hour, then the reaction solution was directly purified on silica gel (EtOAc:hexanes=1:1) to afford the desired product as a pale yellow solid. 1H NMR (CDCl3): δ 7.87 (2H, d, J=8.8 Hz), 7.12 (2H, d, J=8.8 Hz), 6.62 (1H, s), 5.05 (2H, s), 3.61 (4H, m), 3.39 (4H, m), 3.04 (3H, s), 2.78 (2H, d, J=6.8 Hz), 2.32 (1H, m), 1.12 (6H, d, J=6.8 Hz).

Workup

  1. customthe reaction solution was directly purified on silica gel (EtOAc:hexanes=1:1)

Sources & evidence

ORD record
ord-af598754551d4285babbef7f73f823e6
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

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