Trifluoroacetic acid → HCID 67966943, compound

HRID 527523Notes

Reaction equation

HRID 527523 reaction equation
CC([N:5]([C:9]([CH3:31])([CH3:30])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[C:25]3[C:26]([CH3:29])=[N:27][O:28][C:24]=3[CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)=[O:11])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:31][C:9]([C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[C:25]3[C:26]([CH3:29])=[N:27][O:28][C:24]=3[CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)=[O:11])([CH3:30])[NH2:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86698413HCID 86698413, compound2×

Product 1

HCID 67966943HCID 67966943, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-dimethylethyl[1,1-dimethyl-2-({4-[(3-methyl-1,2-benzisoxazol-4-yl)oxy]phenyl}amino)-2-oxoethyl]carbamate (Intermediate 24, 34 mg) was dissolved in 4.0 ml of dichloromethane and then TFA (1.0 ml) was added. The reaction mixture was stirred at room temperature for 1 hour. After removal of the volatiles, the residue was charged on a SCX cartridge and eluted successively with dichloromethane, MeOH, NH3 (2.0 M solution in MeOH). Evaporation afforded 18 mg of the title compound.

Workup

  1. customAfter removal of the volatiles
  2. additionthe residue was charged on a SCX cartridge
  3. washeluted successively with dichloromethane, MeOH, NH3 (2.0 M solution in MeOH)
  4. customEvaporation

Sources & evidence

ORD record
ord-e55ee3aca0e447efb10f6e46969baec3
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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