Isoniazid → Ethyl 3-pyridin-4-yl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

HRID 732153

Reaction equation

HRID 732153 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]3[CH2:14][CH2:13][CH2:12][C:9]3=[N:10][N:11]=2)=[CH:3][CH:2]=1.O=C1[CH:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])CCCN1.C(NN)(=O)C1C=CN=CC=1>C(Cl)Cl.CCO>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[N:8]3[CH2:14][CH2:13][CH2:12][CH:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:9]3=[N:10][N:11]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 3767IsoniazidHCID 977733-Carbethoxy-2-piperidoneHCID 8531463-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole

Product 1

HCID 57837993Ethyl 3-pyridin-4-yl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared analogous to 3-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole from ethyl 2-oxopiperidine-3-carboxylate (2.57 g, 15 mmol), Me3OBF4 (2.66 g, 18 mmol) and isonicotinic hydrazide (2.06 g, 15 mmol) in DCM (150 ml) and EtOH (16 ml). Recrystallization from EA afforded 1.67 g (41%). 1H NMR: 1.29 (t, 3 H), 2.03 (m, 1 H), 2.14-2.25 (m, 2 H), 2.32 (m, 1 H), 4.01-4.12 (m, 1 H), 4.16-4.27 (m, 4 H), 7.64 (d, 2 H), 8.74 (d, 2 H)

Workup

  1. customRecrystallization from EA
  2. customafforded 1.67 g (41%)

Sources & evidence

ORD record
ord-8056011aca7c45338bb19f47a7f7734a
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Linked notes

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