1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Pyrazol-1-yl-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

HRID 277122Notes

Reaction equation

HRID 277122 reaction equation
CS([C:4]1[N:19]=[C:7]2[CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[CH:10]=[C:11]([NH2:12])[N:6]2[N:5]=1)=O.[N:20]12[CH2:30][CH2:29][CH2:28][N:27]=C1CCCCC2.C(OC(=O)C)C.CO>N1C=CC=N1>[N:20]1([C:4]2[N:19]=[C:7]3[CH:8]=[C:9]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=4)[CH:10]=[C:11]([NH2:12])[N:6]3[N:5]=2)[CH:30]=[CH:29][CH:28]=[N:27]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21584119Ethylacetate methanolHCID 226297032-Methanesulfinyl-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Product 1

HCID 98820822-Pyrazol-1-yl-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamineYield 26%

Reagents, catalysts & solvents 1

HCID 1048PyrazoleSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.50 g (0.002 mol) 2-methanesulfinyl-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine and 0.33 ml (0.002 mol) 1,8-diazabicyclo[5.4.0]undec-7-en in 12.5 g molten pyrazole as solvent was stirred overnight at 120° C. Destillation of the solvent and chromatography on silicagel with ethylacetate/methanol 95/5 gave 0.13 g (26%) 2-pyrazol-1-yl-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine as a white solid, MS m/e (%):278 (M+H+,100).

Sources & evidence

ORD record
ord-1d2e71b1dc364b6083a5cb32c5ab947d
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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