Diisopropylethylamine → Methyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}-4-ethyl-1,3-thiazole-5-carboxylate

HRID 43886

Reaction equation

HRID 43886 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:14]1[S:15][C:16]([C:21]([O:23][CH3:24])=[O:22])=[C:17]([CH2:19][CH3:20])[N:18]=1.C(N(C(C)C)CC)(C)C>>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][N:11]([C:14]2[S:15][C:16]([C:21]([O:23][CH3:24])=[O:22])=[C:17]([CH2:19][CH3:20])[N:18]=2)[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 15194053-Aminoazetidine, 3-BOC protectedHCID 67549789Methyl 2-bromo-4-ethylthiazole-5-carboxylate

Product 1

HCID 67548731Methyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}-4-ethyl-1,3-thiazole-5-carboxylateYield 66.5%

Procedure

The same operation as in Example (217a) was performed using 3-tert-butoxycarbonylaminoazetidine (124 mg, 0.72 mmol), methyl 2-bromo-4-ethyl-1,3-thiazole-5-carboxylate obtained in Example (22c) (158 mg, 0.63 mmol) and diisopropylethylamine (0.21 mL, 1.20 mmol), to obtain 143 mg of the title compound as a white solid (66%).

Sources & evidence

ORD record
ord-d9ac8d2a62ea482abb80bb757121b7a3
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Linked notes

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