tert-Butyl 8-(cyclopropylmethylene)-2-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[1,5-alpha]pyrazine-7(8H)-carboxylate → 7-N-(tert-Butoxycarbonyl)-8-(cyclopropylmethyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine

HRID 133071Notes

Reaction equation

HRID 133071 reaction equation
[CH:1]1([CH:4]=[C:5]2[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:8][N:7]3[N:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[N:20]=[C:6]23)[CH2:3][CH2:2]1>[Pd].C(O)C>[C:14]([O:13][C:11]([N:10]1[CH2:9][CH2:8][N:7]2[N:18]=[C:19]([C:21]([F:23])([F:22])[F:24])[N:20]=[C:6]2[CH:5]1[CH2:4][CH:1]1[CH2:2][CH2:3]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 1

HCID 69362860tert-Butyl 8-(cyclopropylmethylene)-2-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[1,5-alpha]pyrazine-7(8H)-carboxylate

Product 1

HCID 693628567-N-(tert-Butoxycarbonyl)-8-(cyclopropylmethyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 50 mg (0.15 mmol) of tert-butyl 8-(cyclopropylmethylene)-2-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[1,5-α]pyrazine-7(8H)-carboxylate and 25 mg of 10% palladium on carbon in 0.5 mL of ethanol was stirred under an atmosphere of hydrogen overnight. The mixture was filtered and the filtrate concentrated to give the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-6a3bab5b9a1c468db54c05a079a7cbaa
Source dataset
uspto-grants-2008_06
Patent number
US07390809B2

Reaction notes

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