HCID 178512052, compound → 7-Chloro-2-(5-cyclopropylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

HRID 717556Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[NH:19])[C:10]2[CH:15]=[C:14]([CH:16]3[CH2:18][CH2:17]3)[CH:13]=[N:12][CH:11]=2)[CH:3]=1>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:19]=[C:9]([C:10]3[CH:11]=[N:12][CH:13]=[C:14]([CH:16]4[CH2:18][CH2:17]4)[CH:15]=3)[N:8]=[C:4]2[CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Lead tetra acetate (0.684 g, 0.0015 mol) was added to a solution of N-(4-chloropyridin-2-yl)-5-cyclopropylnicotinimidamide (42-1; 0.280 g, 0.001 mol) in toluene (30 mL) in a 40 mL microwave vial at RT. The reaction mixture was heated to 150° C. for 2 h under microwave irradiation. It was cooled to RT then diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over sodium sulphate and concentrated under vacuum to afford the crude product, which was purified by silica gel column chromatography to afford the title compound. 1H NMR (400 MHz, DMSO) δ 9.08-9.02 (t, J=7.2 Hz, 2H), 8.52 (s, 1H), 8.10-8.05 (d, J=18.4 Hz, 2H), 7.32-7.31 (d, J=6.8 Hz, 1H), 2.08 (s, 1H), 1.07-1.05 (d, J=10.4 Hz, 2H), 0.82-0.81 (d, J=4.4 Hz, 2H). MS (M+1): 271.7.

Workup

temperatureIt was cooled to RT
extractionextracted with ethyl acetate (2×50 mL)
dry with materialThe combined organic layer was dried over sodium sulphate
concentrationconcentrated under vacuum
customto afford the crude product, which
customwas purified by silica gel column chromatography

Sources & evidence

ORD record: ord-e527f1541bc045ce92dff6f57faa59dd
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193724B2

Reaction notes

Loading…