Tetrahydrofuran → HCID 58374619, compound
Reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].C1(P([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C1C=CC([C:41]2[C:42]3[N:43]([N:47]=[C:48]([NH:50][C:51]([CH:53]4[CH2:55][CH2:54]4)=[O:52])[N:49]=3)[CH:44]=[CH:45][CH:46]=2)=CC=1)=O.[CH2:56]1[CH2:60]OC[CH2:57]1>>[N:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][CH2:1][C:2]1[CH:5]=[CH:60][C:56]([C:44]2[N:43]3[N:47]=[C:48]([NH:50][C:51]([CH:53]4[CH2:54][CH2:55]4)=[O:52])[N:49]=[C:42]3[CH:41]=[CH:46][CH:45]=2)=[CH:57][CH:3]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
Potassium tert-butoxide (1.3 eq.) was added to an ice-cooled solution of 2-[(triphenyl-λ5-phosphanyl)-methyl]-pyridine (1.1 eq.) in THF (10 mL/mmol). The resulting mixture was stirred for 30 min at 0° C., then at room temperature for another 30 min. A solution of cyclopropanecarboxylic acid [8-(4-formyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amide (1 eq.) in THF (10 mL/mmol) was added dropwise to the reaction mixture. The stirring was maintained for 8 hrs. The reaction was then quenched with water and extracted with ethyl actate. The organic phase was dried aver MgSO4, filtered and removed under vacuum. The solid was washed with methanol to afford the title compound in 69% yield.
Workup
- waitat room temperature for another 30 min
- temperatureThe stirring was maintained for 8 hrs
- customThe reaction was then quenched with water
- extractionextracted with ethyl actate
- dry with materialThe organic phase was dried aver MgSO4
- filtrationfiltered
- customremoved under vacuum
- washThe solid was washed with methanol
Sources & evidence
- ORD record
- ord-9dd2394376544287b3ed1ba7f589ea9a
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853240B2
Reaction notes
Loading…