Trifluoroacetic acid → HCID 57917610, compound

HRID 1878375Notes

Reaction equation

HRID 1878375 reaction equation
[C:1]([NH:5][C:6]([C:8]1[CH:9]=[C:10]([CH:34]=[CH:35][CH:36]=1)[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]([C:20]2[N:21]=[CH:22][C:23]([NH:26]C(=O)OC(C)(C)C)=[N:24][CH:25]=2)=[O:19])[CH2:14][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[NH2:26][C:23]1[CH:22]=[N:21][C:20]([C:18]([N:15]2[CH2:16][CH2:17][N:12]([CH2:11][C:10]3[CH:9]=[C:8]([CH:36]=[CH:35][CH:34]=3)[C:6]([NH:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:14]2)=[O:19])=[CH:25][N:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57917717HCID 57917717, compound

Product 1

HCID 57917610HCID 57917610, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 5-(1-(3-(tert-butylcarbamoyl)benzyl)piperazine-4-carbonyl)pyrazin-2-ylcarbamate (Example 30;120 mg, 0.242 mmol), dichloromethane (2 mL) and trifluoroacetic acid (2 mL) was stirred at room temperature for 3 hours and was then concentrated under vacuum. The residue was triturated with diethyl ether and then gravity filtered over fluted paper. The collected solid was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate. The aqueous layer was separated and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under vacuum to afford the title compound (89 mg). MS (ESI) m/z 397.2 [M-+H]+

Workup

  1. concentrationwas then concentrated under vacuum
  2. customThe residue was triturated with diethyl ether
  3. filtrationgravity filtered
  4. customThe collected solid was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate
  5. customThe aqueous layer was separated
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined organic layers were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4d34a0fd7b094964be8ca2e729d4e87b
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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