Diisopropylethylamine → Ethyl 2-(4-aminopiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate

HRID 43931

Reaction equation

[NH2:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[C:9]1[S:10][C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:12]([CH3:14])[N:13]=1.C(N(C(C)C)CC)(C)C>>[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:9]2[S:10][C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:12]([CH3:14])[N:13]=2)[CH2:4][CH2:3]1

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 4243614-Piperidinamine

HCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 67548556Ethyl 2-(4-aminopiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylateYield 87.6%

Procedure

The same operation as in Example (237a) was performed using 4-aminopiperidine (0.19 mL, 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 283 mg of the title compound as a pale yellow oily substance (88%).

Sources & evidence

ORD record: ord-73afe5373f8742218418f04cf9ebd489
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Linked notes

Loading…