3-Pyridinecarbonyl chloride, hydrochloride (1:1) → N-(6-bromo-5-methyl[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide

HRID 2382859Notes

Reaction equation

HRID 2382859 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:9]=[C:10]([NH2:12])[N:11]=2)[C:7]=1[CH3:8].Cl.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:9]=[C:10]([NH:12][C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=3)[N:11]=2)[C:7]=1[CH3:8]

Participants

3

Reactant 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 252161856-Bromo-5-methyl[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 25214732N-(6-bromo-5-methyl[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide

Procedure

The title compound was prepared following procedure described for intermediate B1, but starting from 6-bromo-5-methyl[1,2,4]triazolo[1,5-a]pyridin-2-amine ((A8), 4.0 g; 17.62 mmol; 1.0 eq.) and nicotinoyl chloride hydrochloride (3.76 g; 21.1 mmol; 1.2 eq.) as a yellow solid (4.53 g; 77%). 1H NMR (DMSO-d6) δ 11.54 (s, 1H), 9.13 (d, J=2.3 Hz, 1H), 9.78 (dd, J=4.9, 1.5 Hz, 1H), 8.34 (dt, J=7.9, 1.8 Hz, 1H), 7.85 (d, J=8 Hz, 1H), 7.63-7.54 (m, 2H), 2.8 (s, 3H). HPLC, Rt: 1.75 min. (purity 98.8%). LC/MS, M+(ESI): 334.2. CHN analysis: [C13H10N5OBr.1.0H20] Corrected: C, 44.59%; H, 3.45%; N, 20.00%. Found: C, 44.68%; H, 3.41%; N, 19.97%.

Sources & evidence

ORD record
ord-eb8e86265da94a97aa8a0bfd3bc291f1
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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