Reaktion #1981898

Reaktionsgleichung

1-(5-methyl-1,3,4-thiadiazol-2-yl)methanamine hydrochloride

diisopropylethylamine

DMF 3

4-(2,4,6-trifluorobenzoyl)-1-H-pyrrole-2-carboxylic acid

4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxylic acid

Intermediate 1

4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxylic acid

1-hydroxybenzotriazole hydrate

N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide-hydrochloride

→

title compound

Ausbeute 69.3%

N-[(5-methyl-1,3,4-thiadiazol-2-yl)methyl]-4-(2,4,6-trifluorobenzoyl)-1-H-pyrrole-2-carboxamide

Ausbeute 69.3%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Einengenconcentrated
3. 3
   Sonstigechromatographed on silica gel eluting with AcOEt

Vorschrift

To a DMF 3 mL solution of 4-(2,4,6-trifluorobenzoyl)-1-H-pyrrole-2-carboxylic acid (Intermediate 1) (30 mg, 0.11 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (22 mg, 0.15 mmol) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide-hydrochloride (EDC-hydrochloride)(28 mg, 0.15 mmol). The reaction was stirred for 45 min before 1-(5-methyl-1,3,4-thiadiazol-2-yl)methanamine hydrochloride (19 mg, 0.17 mmol) and diisopropylethylamine (0.1 mL, 0.55 mmol) were added. The reaction mixture was stirred at rt overnight, concentrated and chromatographed on silica gel eluting with AcOEt to give the title compound 29 mg.

Quelle