Trifluoroacetic acid → HCID 67236698, compound

HRID 1505360Notes

Reaction equation

HRID 1505360 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][C:17]1[N:22]=[CH:21][C:20]([NH:23][C:24](=[O:36])[C:25]([NH:28]C(=O)OC(C)(C)C)([CH3:27])[CH3:26])=[CH:19][CH:18]=1)[CH3:9]>ClCCl>[CH2:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][C:17]1[N:22]=[CH:21][C:20]([NH:23][C:24](=[O:36])[C:25]([CH3:27])([CH3:26])[NH2:28])=[CH:19][CH:18]=1)[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68322478HCID 68322478, 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 25 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 25 mL of MeOH
  6. customThe ammonia eluate was evaporated under vacuum

Sources & evidence

ORD record
ord-3927a9e76dae469bacb8d69c36f6a42a
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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