1-Bromo-3-chloropropane → 7-(3-Chloropropyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine

HRID 712380Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[N:7]2[CH2:8][CH2:9][NH:10][CH2:11][C:6]2=[N:5][N:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][CH2:23][Cl:24]>CN(C=O)C.O>[Cl:24][CH2:23][CH2:22][CH2:21][N:10]1[CH2:9][CH2:8][N:7]2[C:3]([C:2]([F:12])([F:1])[F:13])=[N:4][N:5]=[C:6]2[CH2:11]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine (1.90 g) in DMF (10 mL) was added K2CO3 (2.35 g) and 1-bromo-3-chloropropane (1.70 mL) at rt. The reaction mixture was heated at 80° C. for 3 h, diluted with water and extracted with ethyl acetate. The combined organic phases were dried over anhydrous Na2SO4 for 1 h, and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 30:1 (v/v) DCM/MeOH) to give the title compound as transparent liquid (0.68 g, 30.00%).

Workup

extractionextracted with ethyl acetate
dry with materialThe combined organic phases were dried over anhydrous Na2SO4 for 1 h
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customthe residue was chromatographed with a silica gel column (eluting agent: 30:1 (v/v) DCM/MeOH)

Sources & evidence

ORD record: ord-7429ed89b7b24ee1b5749ad5dd9ec965
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181277B2

Reaction notes

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