Trifluoroacetic acid → HCID 73295489, compound

HRID 623768Notes

Reaction equation

HRID 623768 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:9]1[C:24]([N:26]1[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[C:28]([CH3:40])([CH3:39])[CH2:27]1)=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([N:8]1[C:12]([C:13]([F:15])([F:14])[F:16])=[CH:11][C:10]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[C:9]1[C:24]([N:26]1[CH2:31][CH2:30][NH:29][C:28]([CH3:40])([CH3:39])[CH2:27]1)=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86711853HCID 86711853, compound

Product 1

HCID 73295489HCID 73295489, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To tert-butyl 4-(1-benzyl-3-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carbonyl)-2,2-dimethylpiperazine-1-carboxylate (103 mg, 0.178 mmol) in DCM (2 mL) was added TFA (0.234 mL, 3.03 mmol). The reaction mixture was stirred for 1 h and then cooled to 0° C. Saturated aqueous NaHCO3 (15 mL) was added. The aqueous layer was separated and extracted twice with DCM (10 mL). The combined organic phases were washed with brine (20 mL) and dried over Na2SO4. Concentration in vacuo was followed by flash chromatography (silica, gradient heptane/EtOAc, 1:0→0:1). Appropriate fractions were combined, solvents removed in vacuo and the product was placed with MeOH (5 mL) in a vial. The remaining oil was dried in vacuo at 40° C. over 6 h. SC-82 (58 mg, 67%) was obtained as a white foam.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted twice with DCM (10 mL)
  3. washThe combined organic phases were washed with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration in vacuo
  6. customsolvents removed in vacuo
  7. customThe remaining oil was dried in vacuo at 40° C. over 6 h
  8. customSC-82 (58 mg, 67%) was obtained as a white foam

Sources & evidence

ORD record
ord-03b876a32c904b13b821fa82b9934b24
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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