Trifluoroacetic acid → HCID 178473709, compound

HRID 2167258Notes

Reaction equation

HRID 2167258 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[N:18](COCC[Si](C)(C)C)[C:17]([CH3:27])=[N:16][CH:15]=3)=[CH:11][CH:12]=2)[CH:7]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[CH2:6][CH:5]1[CH3:36])(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[N:18]=[C:17]([CH3:27])[NH:16][CH:15]=3)=[CH:11][CH:12]=2)[CH:7]([NH:28][C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)[CH2:6][CH:5]1[CH3:36])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 66624791HCID 66624791, compound

Product 1

HCID 178473709HCID 178473709, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[Step 2] 12 mg (cis:trans=3:1) of 1-acetyl-6-{2-methyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-1 H-imidazol-5-yl}-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydroquinoline was dissolved in 1 mL of dichloromethane, and 0.5 mL of trifluoroacetic acid was added to the solution. The mixture was stirred for 3 hours at room temperature. After completion of the reaction, trifluoroacetic acid and dichloromethane were distilled off under reduced pressure. The resulting residue was neutralized with a saturated aqueous solution of sodium hydrogen carbonate, and then was extracted three times with chloroform. The extraction product was dehydrated over anhydrous sodium sulfate, and then was concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (methanol:chloroform=1:10), and thus 9 mg (cis:trans=3:1, 100%) of the title compound was obtained as a yellow solid.

Workup

  1. distillationwere distilled off under reduced pressure
  2. extractionwas extracted three times with chloroform
  3. concentrationwas concentrated under reduced pressure
  4. customThe resulting residue was purified
  5. customwas obtained as a yellow solid

Sources & evidence

ORD record
ord-5086c2bf358e44e397457aabdadeeab8
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

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