Ethyl orthopropionate → 3-Ethyl-7-(4-phenyl-1-piperidinyl)-1,2,4-triazolo[4,3-a]pyridine-8-carbonitrile

HRID 587655Notes

Reaction equation

HRID 587655 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].C(O[C:26](OCC)(OCC)[CH2:27][CH3:28])C>C1(C)C(C)=CC=CC=1>[CH2:27]([C:28]1[N:5]2[CH:6]=[CH:7][C:8]([N:9]3[CH2:10][CH2:11][CH:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:13][CH2:14]3)=[C:3]([C:1]#[N:2])[C:4]2=[N:21][N:22]=1)[CH3:26]

Participants

4

Reactant 2

HCID 66995Ethyl orthopropionateHCID 66787505[3-Cyano-4-(4-phenylpiperidinyl)pyridin-2-yl]-hydrazine

Product 1

HCID 574594753-Ethyl-7-(4-phenyl-1-piperidinyl)-1,2,4-triazolo[4,3-a]pyridine-8-carbonitrile

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of D7 (0.05 g, 0.17 mmol) and triethylorthopropionate (0.462 ml, 2.556 mmol) in xylene (1 ml) was heated in a sealed tube at 180° C. for 2 h. After cooling, the resulting mixture was concentrated in vacuo. The residue thus obtained was triturated with Et2O to yield final compound E10 (0.042 g, 74%).

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-4949993e9e59443c833ef2ec9c840e42
Source dataset
uspto-grants-2016_01
Patent number
US09226930B2

Reaction notes

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