Trifluoroacetic acid → HCID 67236009, compound

HRID 1505329Notes

Reaction equation

HRID 1505329 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][C:10]1[N:15]=[CH:14][C:13]([NH:16][C:17](=[O:28])[C@H:18]([NH:20]C(=O)OC(C)(C)C)[CH3:19])=[CH:12][CH:11]=1.C(O)(C(F)(F)F)=O>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][C:10]1[N:15]=[CH:14][C:13]([NH:16][C:17](=[O:28])[C@@H:18]([CH3:19])[NH2:20])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68322476HCID 68322476, compound2×

Product 1

HCID 67236009HCID 67236009, compoundYield 110.3%

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-06485554a6d14cacb2fb2ede69952df0
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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