4-{2-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-1,3-thiazol-4-yl}benzoic acid → 4-[2-(Piperazin-1-yl)-1,3-thiazol-4-yl]benzoic acid

HRID 606569Notes

Reaction equation

HRID 606569 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[N:11]1([C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH:20]=[CH:21][C:22]([C:25]([OH:27])=[O:26])=[CH:23][CH:24]=3)[N:18]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 181867194-{2-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-1,3-thiazol-4-yl}benzoic acid

Product 1

HCID 670474804-[2-(Piperazin-1-yl)-1,3-thiazol-4-yl]benzoic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

4-[4-(4-Carboxy-phenyl)-thiazol-2-yl]-piperazine-1-carboxylic acid tert-butyl ester (5.0 mmol) was dissolved in hydrochloric acid in dioxane (4N, 25 ml) and the reaction stirred at RT for 2 h. The reaction was concentrated in vacuo to yield 4-(2-piperazin-1-yl-thiazol-4-yl)-benzoic acid. Trimethoxyethane (6.5 mmol) was dissolved in aqueous hydrochloric acid (1N, 10 ml) and the reaction heated at 50° C. for 1.5 h. The reaction was allowed to cool to RT and was then added to a suspension of 4-(2-piperazin-1-yl-thiazol-4-yl)-benzoic acid (5.0 mmol) in acetonitrile (25 ml) and sodium acetate buffer (1N, pH 5.5, 10 ml). The reaction was stirred at RT for 1.5 h. Sodium cyanoborohydride (6.5 mol) was added and the reaction stirred at RT for 16 h. The reaction was concentrated in vacuo and the product purified by flash chromatography (silica gel, 10% methanol in dichloromethane) to give the title product as a colourless oil (0.9 g). m/z=348 (100% M+H) in MS ES+.

Workup

  1. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-810f83bfaf794e67b4c64a5e64c6e029
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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