Trifluoroacetic acid → HCID 57959391, compound

HRID 2091448Notes

Reaction equation

HRID 2091448 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]([N:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[O:14])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[C:1]1([C:7]2[N:8]=[CH:9][C:10]([C:13]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[O:14])=[CH:11][N:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57959394HCID 57959394, compound

Product 1

HCID 57959391HCID 57959391, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture consisting of tert-butyl 4-(2-phenylpyrimidine-5-carbonyl)piperazine-1-carboxylate (587 mg) in dichloromethane (8 mL) at 0° C. was added trifluoroacetic acid (7 mL). The mixture was stirred cold for one hour and was subsequently concentrated under reduced pressure to provide a residue, which was purified by flash silica column chromatography. Elution with 95:5 dichloromethane-methanol with 0.5% concentrated ammonium hydroxide afforded the title compound (400 mg, 94% yield); MS (ESI+) m/z 269 (M+1); HPLC (Column: 2.1×150 mm, 3μGeminiC18; detection wavelength: 210 nm; mobile phase A: 90/10H2O/CH3CN 10 mM NH4OAc; mobile phase B: 10/90H2O/CH3CN 10 mM NH4OAc; gradient: 0-6 minutes 0-100% B, 6-10 minutes 100% B, 10.1-15 minutes 0% B; flow rate: 0.25 mL/min) purity: 98.5%, retention time: 9.7 minutes.

Workup

  1. concentrationwas subsequently concentrated under reduced pressure
  2. customto provide a residue, which
  3. customwas purified by flash silica column chromatography
  4. washElution with 95:5 dichloromethane-methanol with 0.5% concentrated ammonium hydroxide

Sources & evidence

ORD record
ord-117198ef928e41b49d114aebd9a5749c
Source dataset
uspto-grants-2013_05
Patent number
US08440417B2

Reaction notes

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