Trifluoroacetic acid → HCID 22482016, compound

HRID 2182170Notes

Reaction equation

HRID 2182170 reaction equation
C(OC(=O)[N:7]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=1)[C:8]1[N:13]=[C:12]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:11]=[N:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:27][C:23]1[N:22]=[C:21]([CH2:20][NH:7][C:8]2[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[CH:11]=[N:10][CH:9]=2)[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69732637HCID 69732637, compound

Product 1

HCID 22482016HCID 22482016, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (6-methyl-pyridin-2-yl methyl)-(3,4,5,6-tetrahydro-2H-[1,2′]-bipyrazinyl-6′-yl)-carbamic acid tert-butyl ester I-4l (196.9 mg, 0.51 mM) in methylene chloride (2 mL) was treated with trifluoroacetic Acid (0.39 mL, 5.12 mmol). The resulting mixture was stirred at ambient temperature overnight. The reaction mixture was quenched with saturated NaHCO3 solution and the pH of the aqueous layer brought to approximately 10 using 1N NaOH. The reaction mixture was diluted with methylene chloride and separated. The aqueous layer was extracted with methylene chloride and the organic layers were combined, dried (Na2SO4), and concentrated to dryness to afford the desired product I-4m.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 solution
  2. additionThe reaction mixture was diluted with methylene chloride
  3. customseparated
  4. extractionThe aqueous layer was extracted with methylene chloride
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fc1bb2ca3d1e41a6a4b3ed6cf907a6cf
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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