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

HRID 587630Notes

Reaction equation

HRID 587630 reaction equation
[C:1]([C:3]1[C:4]2[N:5]([CH:21]=[N:22][N:23]=2)[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].O(Cl)Cl.[P+5].CN([CH:31]=[O:32])C>>[C:1]([C:3]1[C:4]2[N:5]([C:21]([CH:31]=[O:32])=[N:22][N:23]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:11][CH2:10]1)#[N:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 667888318-Cyano-7-(4-phenylpiperidinyl)[1,2,4]triazolo[4,3-a]pyridineHCID 178479711HCID 178479711, compound

Product 1

HCID 574595958-Cyano-3-formyl-7-(4phenylpiperidinyl)[1,2,4]triazolo[4,3-a]pyridineYield 26%

Procedure

D8 (0.25 g, 0.824 mmol) and phosphorus (V) oxychloride (0.116 ml, 1.236 mmol) in DMF (5 ml) was heated in a sealed tube at 80° C. for 4 h. After cooling, the mixture was concentrated in vacuo. The crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 3% as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D9 (0.070 g, 26%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 3% as eluent)
  4. customThe desired fractions were collected
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc79c8bd42814ccc96c1dc1e2e395d14
Source dataset
uspto-grants-2016_01
Patent number
US09226930B2

Reaction notes

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