Trifluoroacetic acid → HCID 67966862, compound

HRID 527537Notes

Reaction equation

HRID 527537 reaction equation
CC([N:5]([C@@H:9]([C:12]([NH:14][C:15]1[CH:16]=[N:17][C:18]([O:21][C:22]2[C:27]3[C:28]([CH:31]([CH3:33])[CH3:32])=[N:29][O:30][C:26]=3[CH:25]=[CH:24][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>[NH2:5][C@H:9]([CH2:10][CH3:11])[C:12]([NH:14][C:15]1[CH:16]=[N:17][C:18]([O:21][C:22]2[C:27]3[C:28]([CH:31]([CH3:32])[CH3:33])=[N:29][O:30][C:26]=3[CH:25]=[CH:24][CH:23]=2)=[CH:19][CH:20]=1)=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86698420HCID 86698420, compound2×

Product 1

HCID 67966862HCID 67966862, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-dimethylethyl((1R)-1-{[(6-{[3-(1-methylethyl)-1,2-benzisoxazol-4-yl]oxy}-3-pyridinyl)amino]carbonyl}propyl)carbamate (Intermediate 43, 2.0 mg) was dissolved in dichloromethane (1.0 mL) and, at 0° C., TFA (0.05 mL, 0.65 mmol) was added. The reaction mixture was stirred at that temperature for 2 hours. After removal of the volatiles, the residue obtained was charged on a SCX cartridge and eluted with DCM/MeOH/NH3 (2.0 M in MeOH) to afford the title compound.

Workup

  1. customAfter removal of the volatiles
  2. customthe residue obtained
  3. additionwas charged on a SCX cartridge
  4. washeluted with DCM/MeOH/NH3 (2.0 M in MeOH)

Sources & evidence

ORD record
ord-88383b0321c24aab8439378b8d1b2e5a
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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