Diisopropylethylamine → Ethyl 2-{4-[(tert-butoxycarbonyl)(methyl)amino]piperidin-1-yl}-4-methyl-1,3-thiazole-5-carboxylate

HRID 43933Notes

Reaction equation

HRID 43933 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:15])[CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:17]1[S:18][C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:20]([CH3:22])[N:21]=1.C(N(C(C)C)CC)(C)C>>[C:1]([O:5][C:6]([N:8]([CH3:15])[CH:9]1[CH2:10][CH2:11][N:12]([C:17]2[S:18][C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:20]([CH3:22])[N:21]=2)[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 27568064-N-Boc-4-N-Methyl-aminopiperidineHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 67549045Ethyl 2-{4-[(tert-butoxycarbonyl)(methyl)amino]piperidin-1-yl}-4-methyl-1,3-thiazole-5-carboxylateYield 87.6%

Procedure

The same operation as in Example (217a) was performed using 4-[(tert-butoxycarbonyl)(methyl)amino]piperidine (386 mg, 1.80 mmol), ethyl 2-bromo-4-methylthiazole-5-carboxylate (300 mg, 1.20 mmol) and diisopropylethylamine (0.42 mL, 2.40 mmol), to obtain 403 mg of the title compound as a colorless oily substance (88%).

Sources & evidence

ORD record
ord-10e9d64b4d61479ba23b352b6e6042ff
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

Loading…