Trifluoroacetic acid → HCID 67236698, compound

HRID 1023560Notes

Reaction equation

HRID 1023560 reaction equation
FC(F)(F)C(O)=O.CC([N:12]([C:16]([CH3:36])([CH3:35])[C:17]([NH:19][C:20]1[CH:21]=[N:22][C:23]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH2:33][CH3:34])=[CH:24][CH:25]=1)=[O:18])C(=O)[O-])(C)C>ClCCl>[CH2:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[O:26][C:23]1[N:22]=[CH:21][C:20]([NH:19][C:17](=[O:18])[C:16]([CH3:36])([CH3:35])[NH2:12])=[CH:25][CH:24]=1)[CH3:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131731387HCID 131731387, compound2×

Product 1

HCID 67236698HCID 67236698, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round-bottomed flask 1,1-dimethylethyl[2-({6-[(2-ethylphenyl)oxy]-3-pyridinyl}amino)-1,1-dimethyl-2-oxoethyl]carbamate (Intermediate 77, 88.6 mg) was dissolved in dichloromethane (2 mL) to give a yellow solution. Trifluoroacetic acid (2 mL, 26.0 mmol) was added. The reaction mixture was stirred at room temperature. After 20 minutes, the solvent was evaporated under vacuum affording a yellow oil that was charged on a 5 g SCX cartridge and was then flushed with mL of MeOH followed by 25 mL of 2M solution of ammonia in MeOH. The ammonia eluate was evaporated under vacuum to afford the title compound as a yellow oil which solidified (67.1 mg).

Workup

  1. customto give a yellow solution
  2. customthe solvent was evaporated under vacuum
  3. customaffording a yellow oil that
  4. additionwas charged on a 5 g SCX cartridge
  5. customwas then flushed with mL of MeOH
  6. customThe ammonia eluate was evaporated under vacuum

Sources & evidence

ORD record
ord-52d74342bbf64399b774e6fd8aca94e2
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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