Trifluoroacetic acid → HCID 67235584, compound

HRID 527724Notes

Reaction equation

HRID 527724 reaction equation
CC([N:5]([C@@:9]([CH3:31])([C:12]([NH:14][C:15]1[CH:16]=[N:17][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[C:24]([O:29][CH3:30])[CH:23]=2)=[CH:19][CH:20]=1)=[O:13])[CH2:10][CH3:11])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][C:18]2[N:17]=[CH:16][C:15]([NH:14][C:12](=[O:13])[C@:9]([CH3:31])([CH2:10][CH3:11])[NH2:5])=[CH:20][CH:19]=2)=[CH:23][C:24]=1[O:29][CH3:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86673600HCID 86673600, compound

Product 1

HCID 67235584HCID 67235584, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl((1R)-1-methyl-1-{[(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)amino]carbonyl}propyl)carbamate (Reference Intermediate R7, 65 mg) in dry dichloromethane (3 mL) cooled to 0° C., TFA (0.700 mL, 9.08 mmol) was added dropwise. The reaction was stirred at that temperature for 2 hours. The reaction was quenched with a saturated aqueous solution of NaHCO3 (20 mL) added at 0° C., and extracted with dichloromethane (3×7 mL). The combined organic layers were dried over sodium sulphate, filtered and evaporated to afford the title compound as a white solid (44 mg).

Workup

  1. customThe reaction was quenched with a saturated aqueous solution of NaHCO3 (20 mL)
  2. additionadded at 0° C.
  3. extractionextracted with dichloromethane (3×7 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ede002750cb54e158d91c9ffee1706e2
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

Loading…