Ammonia → 3-Amino-1-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one

HRID 445962Notes

Reaction equation

C1COCC1.[BH4-].[Na+].[O:8]=[C:9]([N:23]1[CH2:28][CH2:27][N:26]2[C:29]([C:32]([F:35])([F:34])[F:33])=[N:30][N:31]=[C:25]2[CH2:24]1)[CH:10]=[C:11]([NH2:22])[CH2:12][C:13]1[CH:18]=[C:17]([F:19])[C:16]([F:20])=[CH:15][C:14]=1[F:21].N>O.C(O)(=O)C>[O:8]=[C:9]([N:23]1[CH2:28][CH2:27][N:26]2[C:29]([C:32]([F:35])([F:34])[F:33])=[N:30][N:31]=[C:25]2[CH2:24]1)[CH2:10][CH:11]([NH2:22])[CH2:12][C:13]1[CH:18]=[C:17]([F:19])[C:16]([F:20])=[CH:15][C:14]=1[F:21]

Participants

Conditions

Temperature: -7.5 °C

Procedure

In a 250 mL round bottom flask dry THF (35 mL) was taken. It was cooled to −10 to −5° C. and NaBH4 (2.0 g) was added. After that acetic acid (33.7 mL) was added dropwise at −5 to 0° C. over a period of 15-30 min. 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazol o[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine (5.0 g) was added into the reaction mixture, keeping the temperature between −2 to 0° C. It was stirred for 2-3 h at −5 to 0° C. Reaction mixture was poured into cold water. It was basified by adding aq. ammonia solution. Product was extracted in ethyl acetate. The organic layer was collected. It was washed with water and dried over anhydrous sodium sulfate. Solvent was evaporated at reduced pressure to obtain the product. (Wt.-4.2 g, % Y-83.6%, % Purity by HPLC-60.1%).

Workup

custombetween −2 to 0° C
customReaction mixture
extractionProduct was extracted in ethyl acetate
customThe organic layer was collected
washIt was washed with water
dry with materialdried over anhydrous sodium sulfate
customSolvent was evaporated at reduced pressure
customto obtain the product

Sources & evidence

ORD record: ord-492bd191faaa4649903f46372ba60c4d
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476437B2

Reaction notes

Loading…