Formamide → 8-(3,4-Difluorobenzyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide

HRID 1398153Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[F:37])[CH2:5][C:6]1([C:29]([O:31]CC)=O)[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][C:24]([CH3:26])=[N:23][CH:22]=4)=[C:17]([O:27][CH3:28])[CH:16]=3)=[N:13][N:14]=[C:7]12.C([NH2:40])=O.C[O-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[F:37])[CH2:5][C:6]1([C:29]([NH2:40])=[O:31])[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][C:24]([CH3:26])=[N:23][CH:22]=4)=[C:17]([O:27][CH3:28])[CH:16]=3)=[N:13][N:14]=[C:7]12

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of ethyl 8-(3,4-difluorobenzyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (100 mg), formamide (78.5 μL), sodium methoxide (28% methanol solution, 200 μL) and DMF (1 mL) was stirred at 70° C. for 30 min, and allowed to cool to room temperature. Saturated aqueous ammonium chloride solution was added. The precipitate was collected by filtration, washed with water and IPE, and dried under reduced pressure to give the title compound (80.4 mg).

Workup

temperatureto cool to room temperature
filtrationThe precipitate was collected by filtration
washwashed with water and IPE
customdried under reduced pressure

Sources & evidence

ORD record: ord-e0af0ffbed0645799928083c76c02aa1
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901309B2

Reaction notes

Loading…