1-Hydroxybenzotriazole → HCID 44235032、化合物

DIPEA (200 mg, 1.5 mmol) was added to a stirred solution of 5-(5-chloro-thiophen-2-yl)-1H-pyrazole-3-carboxylic acid (100 mg, 0.44 mmol) (prepared by the method used for the synthesis of Intermediate 29, starting from 2-acetyl-5-chlorothiophene) in DMF (2 mL) followed by HOBt (63 mg, 0.46 mmol) and EDCI.HCl (90 mg, 0.46 mmol). After 5 minutes 2-amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (140 mg, 0.44 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added to the reaction mixture and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with cold water, extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure. Purification by recrystallisation from 10% EtOAc in hexane afforded 146 mg (65.1% Yield) of 5-(5-chloro-thiophen-2-yl)-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 513, 98.3%. 1H NMR (300 MHz, DMSO-d6): δ 13.7 (s, 1H), 8.64 (m, 1H), 7.5 (t, 1H), 7.3 (m, 3H), 7.2 (m, 2H), 6.9 (m, 1H), 4.7 (m, 1H), 4.2 (m, 2H), 3.9 (m, 1H), 3.7 (m, 1H), 3.4 (m, 1H), 3.3 (m, 1H), 1.9 (m, 2H), 1.6 (m, 2H).

1. customprepared by the method
2. additionwas added to the reaction mixture
3. extractionextracted with ethyl acetate
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customPurification
7. customby recrystallisation from 10% EtOAc in hexane

ORDレコード

ord-afc3eba0885b4985b1e90bbaf01a2cf6

出典データセット

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08129376B2