Diisopropylethylamine → Ethyl 2-(4-(tert-butoxycarbonyl)piperazin-1-YL)thiazole-4-carboxylate

HRID 2063417Notes

Reaction equation

HRID 2063417 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](Br)[S:9][CH:10]=1)=[O:5])[CH3:2].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C>O1CCOCC1>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:8]2[S:9][CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylate

Product 1

HCID 53418800Ethyl 2-(4-(tert-butoxycarbonyl)piperazin-1-YL)thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-bromo-thiazole-4-carboxylic acid ethyl ester (1.4 g, 5.93 mmol), piperazine-1-carboxylic acid tert-butyl ester (1.16 g, 1.05 eq.) and DIPEA (1.15 g, 1.5 eq.) in 1,4-dioxane (20 mL) was heated to reflux overnight. After cooling, the solvent was removed in vacuo. The crude product was purified on silica gel (EtOAc:hexanes=1:4) to afford the desired product as a pale yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. temperatureAfter cooling
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified on silica gel (EtOAc:hexanes=1:4)

Sources & evidence

ORD record
ord-e701b2daf5344184b093ca7c225cca34
Source dataset
uspto-grants-2012_10
Patent number
US08288384B2

Reaction notes

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