Hydrochloric Acid → 3'-(2-Fluoro-3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine

HRID 220440Notes

Reaction equation

HRID 220440 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[C:22]=3[F:31])=[N:19][CH:18]=[CH:17][N:16]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>O1CCOCC1.C(Cl)Cl>[F:31][C:22]1[C:23]([C:27]([F:30])([F:28])[F:29])=[CH:24][CH:25]=[CH:26][C:21]=1[C:20]1[C:15]([N:12]2[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]2)=[N:16][CH:17]=[CH:18][N:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 687379823'-(2-Fluoro-3-trifluoromethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid t-butyl ester

Product 1

HCID 685952853'-(2-Fluoro-3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 4 M HCl in 1,4-dioxane (5 mL) to a solution of 3′-(2-fluoro-3-trifluoromethyl-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid t-butyl ester (0.101 g, 0.237 mmol) in DCM (10 mL) and stir for 19 hr. Concentrate, dissolve the residue in methanol (20 mL) and purify by SCX chromatography (pre-wash column with methanol), load material, elute with 2 M ammonia in methanol, and concentrate to give the title preparation as a yellow solid (0.0985 g). MS (ES): m/z=327 [M+H]+.

Workup

  1. concentrationConcentrate
  2. dissolutiondissolve the residue in methanol (20 mL)
  3. custompurify by SCX chromatography (pre-wash column with methanol), load material
  4. washelute with 2 M ammonia in methanol
  5. concentrationconcentrate
  6. customto give the title

Sources & evidence

ORD record
ord-0d3f75f4ffed43fcb9d84f6d73f50045
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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