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 445959Notes

Reaction equation

HRID 445959 reaction equation
O1CCCC1.B.N1CCCCC1.CS(O)(=O)=O.[O:18]=[C:19]([N:33]1[CH2:38][CH2:37][N:36]2[C:39]([C:42]([F:45])([F:44])[F:43])=[N:40][N:41]=[C:35]2[CH2:34]1)[CH:20]=[C:21]([NH2:32])[CH2:22][C:23]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=1[F:31].N>O>[O:18]=[C:19]([N:33]1[CH2:38][CH2:37][N:36]2[C:39]([C:42]([F:45])([F:44])[F:43])=[N:40][N:41]=[C:35]2[CH2:34]1)[CH2:20][CH:21]([NH2:32])[CH2:22][C:23]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=1[F:31]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 6395Methanesulfonic AcidHCID 8082PiperidineHCID 2723981Borane;tetrahydrofuranHCID 534002733-Amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

Product 1

HCID 113066913-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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

In a 250 mL round bottom flask 1.0 M Borane tetrahydrofuran (37 mL) was taken. It was cooled to −10° C. and piperidine (3.14 g) was added dropwise at −10 to 5° C. After 30 min. methanesulfonic acid (6.0 mL) was added dropwise at −10 to 5° C. over a period of 15-30 min. Separately, 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine (5.0 g) was added in small portions into the reaction mixture, keeping the temperature between −10 to −5° C. It was stirred for 1 h at −10 to −5° C. Reaction mixture was poured into cold water. It was basified by adding aq. ammonia solution. Product was extracted in an 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.-4.1 g, % Y-81.0%, % Purity by HPLC-84.5%).

Workup

  1. custombetween −10 to −5° C
  2. customReaction mixture
  3. extractionProduct was extracted in an ethyl acetate
  4. customThe organic layer was collected
  5. washIt was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customSolvent was evaporated at reduced pressure
  8. customto obtain the product

Sources & evidence

ORD record
ord-f8e3152660ba4e83b7a0150af40e206c
Source dataset
uspto-grants-2013_07
Patent number
US08476437B2

Reaction notes

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