HCID 661622, compound → 1-Phenyl-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridine

HRID 2177582Notes

Reaction equation

HRID 2177582 reaction equation
[C:1]1([N:7]2[C:15]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.O=[Pt]=O>[C:1]1([N:7]2[C:15]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[N:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 661622HCID 661622, compound

Product 1

HCID 11082791-Phenyl-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridineYield 56.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-phenyl-1H-[1,2,3]triazolo[4,5-c]pyridine (61 mg, 0.31 mmol) in MeOH (15 ml) was passed through a PtO2 catalyst cartridge on an H-Cube hydrogenation apparatus at a pressure of 70 bar and a flow rate of 1 ml/min. The reaction was concentrated and the crude reaction mixture purified on 12 g SiO2 column with 0-8% NH3/MeOH CH2Cl2 to give 35 mg (56%) of 1-phenyl-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridine. MS (ESI): mass calcd. for C11H12N4, 200.2. m/z found, 201.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.99 (dt, J=8.0, 1.1 Hz, 2H), 7.61-7.50 (m, 2H), 7.48-7.41 (m, 2H), 7.33-7.27 (m, 1H), 4.14-4.07 (m, 2H), 3.20 (t, J=5.9 Hz, 2H), 2.88 (t, J=5.9 Hz, 2H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe crude reaction mixture
  3. custompurified on 12 g SiO2 column with 0-8% NH3/MeOH CH2Cl2

Sources & evidence

ORD record
ord-edae7c60b71942c1a5e402f7e454a76e
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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