Methanesulfonyl chloride → Tert-butyl 4-[4-(chloromethyl)-1,3-thiazol-2-YL]piperazine-1-carboxylate

HRID 1869494Notes

Reaction equation

HRID 1869494 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][CH:16]=[C:17]([CH2:19]O)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.CS([Cl:34])(=O)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][CH:16]=[C:17]([CH2:19][Cl:34])[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 574237984-(4-Hydroxymethyl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 18186678Tert-butyl 4-[4-(chloromethyl)-1,3-thiazol-2-YL]piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-hydroxymethyl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (848 mg, 2.83 mmol) and DIPEA (550 mg, 1.5 eq.) in CH2Cl2 (10 mL) was added MsCl (285 □L, 1.3 eq.) dropwise. The resulting mixture was stirred overnight. The reaction solution was then concentrated in vacuo. The crude product was purified on silica gel (EtOAc:hexanes=1:4) to afford the desired product as an oil.

Workup

  1. concentrationThe reaction solution was then concentrated in vacuo
  2. customThe crude product was purified on silica gel (EtOAc:hexanes=1:4)

Sources & evidence

ORD record
ord-c94beafc5f8b4a0d953cda6b5cfc954b
Source dataset
uspto-grants-2009_12
Patent number
US07638541B2

Reaction notes

Loading…