Ethyl orthoformate → 8-Cyano-7-(4-phenylpiperidinyl)[1,2,4]triazolo[4,3-a]pyridine

HRID 587629Notes

Reaction equation

HRID 587629 reaction equation
[C:1]([C:3]1[C:4]([NH:21][NH2:22])=[N:5][CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)#[N:2].[CH2:23](OC(OCC)OCC)C>C1(C)C(C)=CC=CC=1>[C:1]([C:3]1[C:4]2[N:5]([CH:23]=[N:22][N:21]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:10][CH2:11][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:14]1)#[N:2]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 66787505[3-Cyano-4-(4-phenylpiperidinyl)pyridin-2-yl]-hydrazine

Product 1

HCID 667888318-Cyano-7-(4-phenylpiperidinyl)[1,2,4]triazolo[4,3-a]pyridineYield 90.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

D7 (1 g, 3.409 mmol) and triethylorthoformate (7.577 g, 51.13 mmol) in xylene (25 ml) were heated in a sealed tube at 180° C. for 1 h. After cooling, the resulting mixture was concentrated in vacuo. The residue thus obtained was triturated with Et2O to yield compound D8 (0.932 g, 90%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. customThe residue thus obtained
  4. customwas triturated with Et2O

Sources & evidence

ORD record
ord-cb0830f865244359af3a3873767ab099
Source dataset
uspto-grants-2016_01
Patent number
US09226930B2

Reaction notes

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