Trifluoroacetic acid → HCID 67236009, compound

HRID 1023530Notes

Reaction equation

HRID 1023530 reaction equation
CC([N:5]([C@H:9]([CH3:28])[C:10]([NH:12][C:13]1[CH:14]=[N:15][C:16]([O:19][C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:21]=2[CH3:27])=[CH:17][CH:18]=1)=[O:11])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:27][C:21]1[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:20]=1[O:19][C:16]1[N:15]=[CH:14][C:13]([NH:12][C:10](=[O:11])[C@@H:9]([CH3:28])[NH2:5])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86673584HCID 86673584, compound2×

Product 1

HCID 67236009HCID 67236009, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1,1-dimethylethyl[(1R)-2-({6-[(2,5-dimethylphenyl)oxy]-3-pyridinyl}amino)-1-methyl-2-oxoethyl]carbamate (Intermediate 35, 60 mg) was dissolved in 4 mL of dry dichloromethane. To this solution, at 0° C., were added dropwise 40 equivalents of TFA (0.480 mL). The reaction was stirred for 3 hours 30 at 0° C. The reaction mixture was evaporated and then purified by SCX on a 5 g cartridge. 3 CV of methanol were used first, then the residue was adsorbed on the cartridge, washed with 5 CV of methanol and desorbed with CV of methanolic ammonia (1N). Evaporation of the volatiles, afforded the title compound (49 mg)

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified by SCX on a 5 g cartridge
  3. washwashed with 5 CV of methanol
  4. customEvaporation of the volatiles

Sources & evidence

ORD record
ord-a906627bd8e94f158517aefdf851c77a
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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