Trifluoroacetic acid → N-(3-Chloro-benzyl)-N-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-6'-yl)-acetamide

HRID 2182176Notes

Reaction equation

HRID 2182176 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[N:18][CH:17]=[C:16]([N:20]([C:29](=[O:31])[CH3:30])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][N:20]([C:16]1[N:15]=[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=[N:18][CH:17]=1)[C:29](=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 697323276'-[Acetyl-(3-chloro-benzyl)-amino]-2,3,5,6-tetra-hydro-[1,2']bipyrazinyl-4-carboxylic acid tert-butyl ester

Product 1

HCID 9924306N-(3-Chloro-benzyl)-N-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-6'-yl)-acetamideYield 126.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6′-[acetyl-(3-chloro-benzyl)-amino]-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester I-5c (27.1 mg, 0.06 mmol) in methylene chloride (1 mL) was added trifluoroacetic Acid (1 mL). The reaction mixture was stirred at room temperature until the reaction was completed. The reaction mixture was poured into saturated NaHCO3 (20 mL) and extracted with methylene chloride (2×15 mL). The organic layers were combined, dried (Na2SO4), filtered, and concentrated to dryness to yield the title compound 5-A (26.2 mg).

Workup

  1. extractionextracted with methylene chloride (2×15 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5ac56bed6b7b4a07b2e8365089018aea
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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