Pyridine → N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-2-pyridin-3-ylacetamide

HRID 2382898Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8](Cl)=[O:9])[CH:2]=1.[CH:11]1([NH:17][C:18]2[N:23]3[N:24]=[C:25]([NH2:27])[N:26]=[C:22]3[CH:21]=[CH:20][CH:19]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.N1C=CC=CC=1.CCOCC>C(Cl)Cl.O>[CH:11]1([NH:17][C:18]2[N:23]3[N:24]=[C:25]([NH:27][C:8](=[O:9])[CH2:7][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[N:26]=[C:22]3[CH:21]=[CH:20][CH:19]=2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of pyridin-3-ylacetyl chloride (120.07 mg; 0.77 mmol; 1.50 eq.) and N5-cyclohexyl[1,2,4]triazolo[1,5-a]pyridine-2,5-diamine ((A9); 119 mg; 0.51 mmol; 1.0 eq.) in DCM (1 mL) in presence of pyridine (1244; 1.54 mmol; 3 eq.) was heated in a sealed tube at 55° C. for 3 h. Et2O and Water were then added to the mixture, the precipitate obtained was filtered, washed with water, Et2O, Acetonitrile and dried under vacuum at 40° C. to give the title compound as an off-white powder (74 mg, 41%). HPLC, Rt: 2.49 min. (purity 98.0%). LC/MS, M+(ESI): 350.9, M−(ESI): 348.9.

Workup

customthe precipitate obtained
filtrationwas filtered
washwashed with water, Et2O, Acetonitrile
customdried under vacuum at 40° C.

Sources & evidence

ORD record: ord-55994a2eb7d04a519fd33c1d1c6ec273
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263595B2

Reaction notes

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