N'-(4-benzyloxy-3-cyano-pyridin-2-yl)-2-cyclopropylacetohydrazide → 7-Chloro-3-(cyclopropylmethyl)[1,2,4]triazolo[4,3-a]pyridine-8-carbonitrile
Reaction equation
C(O[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH:15][NH:16][C:17](=O)[CH2:18][CH:19]2[CH2:21][CH2:20]2)[C:10]=1[C:23]#[N:24])C1C=CC=CC=1.O(Cl)[Cl:26].[P+5]>ClCCCl.C(Cl)Cl>[Cl:26][C:9]1[CH:14]=[CH:13][N:12]2[C:17]([CH2:18][CH:19]3[CH2:21][CH2:20]3)=[N:16][N:15]=[C:11]2[C:10]=1[C:23]#[N:24]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 150 °C
Procedure
Intermediate compound D4 (1.4 g, 4.343 mmol) and phosphorous (V) oxychloride (0.810 ml, 8.686 mmol) in DCE (15 ml) were subjected to microwave heating at 150° C. 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
- temperatureAfter cooling
- washwashed with NaHCO3 (aqueous sat. solution)
- customThe organic layer was separated
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2% as eluent)
- customThe desired fractions were collected
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8a1c604bbf544ca99ddcfc41a464a2c9
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716480B2
Reaction notes
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