Trifluoroacetic acid → HCID 67235652, compound

HRID 1023573Notes

Reaction equation

HRID 1023573 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3([NH:22]C(=O)OC(C)(C)C)[CH2:21][CH2:20][CH2:19]3)=[O:17])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[O:30][CH3:31].C(O)(C(F)(F)F)=O>ClCCl>[NH2:22][C:18]1([C:16]([NH:15][C:12]2[CH:13]=[N:14][C:9]([O:8][C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([O:30][CH3:31])[CH:4]=3)=[CH:10][CH:11]=2)=[O:17])[CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68322620HCID 68322620, compound2×

Product 1

HCID 67235652HCID 67235652, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,1-dimethylethyl (1-{[(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)amino]carbonyl}cyclobutyl)carbamate (Intermediate 101, 80 mg) in dry dichloromethane (2 mL) cooled to 0° C. TFA (0.865 mL, 11.23 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 2 hours, it was then allowed to reach room temperature. Dichloromethane and the excess of TFA were evaporated. The residue was diluted with dichloromethane (5 mL) and neutralized with a saturated solution of NaHCO3. The organic layer was separated, dried over sodium sulphate, filtered and evaporated to afford the title as a white solid (60 mg).

Workup

  1. customto reach room temperature
  2. customDichloromethane and the excess of TFA were evaporated
  3. additionThe residue was diluted with dichloromethane (5 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-b0560f0a08b44733a233c3e0c8216a6b
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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