Pyrazole → 7-chloro-5-(1H-pyrazol-1-yl)[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 712360Notes

Reaction equation

HRID 712360 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[C:4]([Cl:12])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:19]1[CH:23]=[CH:22][CH:21]=[N:20]1>CN(C=O)C>[Cl:12][C:4]1[CH:3]=[C:2]([N:19]2[CH:23]=[CH:22][CH:21]=[N:20]2)[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 594375625,7-Dichloro-[1,2,4]triazolo[1,5-A]pyridin-2-amine2×

Product 1

HCID 669773157-chloro-5-(1H-pyrazol-1-yl)[1,2,4]triazolo[1,5-a]pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

5,7-Dichloro[1,2,4]triazolo[1,5-a]pyridin-2-amine (Intermediate 15) (0.5 g, 2.46 mmol), cesium carbonate (1.6 g, 4.93 mmol) and pyrazole (0.5 g, 7.39 mmol) was suspended in DMF (10 mL) and stirred at 70° C. for 2 h after which time LCMS showed desired product formation. The reaction mixture was filtered through celite, which was washed with further DMF and the resultant green/brown solution was concentrated in vacuo to give a brown residue, which was partitioned between 10% IPA/DCM (20 mL) and water (10 mL), the organic layer was separated and the aqueous extracted with further 10% IPA/DCM (2×10 mL). The organic layers were combined and dried (MgSO4), filtered and concentrated in vacuo to give the desired product as a brown solid (0.4 g, 69%). 1H NMR (DMSO) δ 9.16 (d, J=2.6 Hz, 1H), 7.99 (d, J=1.4 Hz, 1H), 7.54 (d, J=2.1 Hz, 1H), 7.36 (d, J=2.1 Hz, 1H), 6.72 (dd, J=2.4, 1.9 Hz, 1H), 6.46 (s, 2H). MS: 235.12 [M+H]+.

Sources & evidence

ORD record
ord-645c1f9aa05e4265a55b432c37aca43b
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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