N'-(4-benzyloxy-3-cyano-pyridin-2-yl)-2-cyclopropylacetohydrazide → 7-Chloro-3-(cyclopropylmethyl)[1,2,4]triazolo[4,3-a]pyridine-8-carbonitrile

HRID 1428487Notes

Reaction equation

HRID 1428487 reaction equation
[C:1]([C:3]1[C:4]([NH:17][NH:18][C:19](=O)[CH2:20][CH:21]2[CH2:23][CH2:22]2)=[N:5][CH:6]=[CH:7][C:8]=1OCC1C=CC=CC=1)#[N:2].O(Cl)[Cl:26].[P+5]>ClCCCl.C(Cl)Cl>[Cl:26][C:8]1[CH:7]=[CH:6][N:5]2[C:19]([CH2:20][CH:21]3[CH2:23][CH2:22]3)=[N:18][N:17]=[C:4]2[C:3]=1[C:1]#[N:2]

Participants

5

Reactant 2

HCID 66784643N'-(4-benzyloxy-3-cyano-pyridin-2-yl)-2-cyclopropylacetohydrazideHCID 178479711HCID 178479711, compound

Product 1

HCID 574595937-Chloro-3-(cyclopropylmethyl)[1,2,4]triazolo[4,3-a]pyridine-8-carbonitrileYield 64.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of D4 (1.4 g, 4.343 mmol) and phosphorous(V)oxychloride (0.810 ml, 8.686 mmol) in DCE (15 ml) was heated at 150° C. under microwave irradiation for 5 min. After cooling, the mixture was diluted with DCM and washed with NaHCO3 (aqueous sat. solution). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2% as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D5 (0.650 g, 64%).

Workup

  1. temperatureAfter cooling
  2. washwashed with NaHCO3 (aqueous sat. solution)
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2% as eluent)
  7. customThe desired fractions were collected
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d701d864225c4df19e61d135e8ccc734
Source dataset
uspto-grants-2015_01
Patent number
US08937060B2

Reaction notes

Loading…