反应详情

DIPEA (167 mg, 1.3 mmol) followed by HOBt (48 mg, 0.35 mmol) and EDCI (124 mg, 0.64 mmol) were added to a stirred solution of [(1-pyridin-3-yl-1H-[1,2,3]triazole-4-carbonyl)-amino]-acetic acid (prepared by the method used for the synthesis of Intermediate 64, starting from 3-aminopyridine, and subsequently, application of Step 3 of the General Scheme) (80 mg, 0.32 mmol) in DMF (2 mL). After 2 minutes of stirring, 3-(2-chloro-phenoxy)-pyrrolidine hydrochloride (prepared by the method used for the synthesis of Intermediate 72) (75.7 mg, 0.32 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was partitioned between cold water and ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. Purification by recrystallisation from a mixture of DCM and hexane afforded 60 mg (43.4% Yield) of 1-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid {2-[3-(2-chloro-phenoxy)-pyrrolidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 427. 1H NMR (300 MHz, DMSO-d6): δ 9.45 (s, 1H), 9.2 (d, 1H), 8.75 (d, 1H), 8.6 (q, 1H), 8.4 (m, 1H), 7.7 (q, 1H), 7.5-7.4 (m, 1H), 7.4-7.2 (m, 2H), 7.06-6.96 (m, 1H), 5.3-5.1 (d, 1H), 4.25-4.0 (m, 2H), 4.0-3.6 (m, 4H), 3.5-3.4 (m, 1H), 2.3-2.2 (m, 1H).

1. customprepared by the method
2. additionwas added
3. stirringthe resulting mixture was stirred at room temperature overnight
4. customThe reaction mixture was partitioned between cold water and ethyl acetate
5. dry with materialThe organic layer was dried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customPurification
8. customby recrystallisation
9. additionfrom a mixture of DCM and hexane