Trifluoroacetic acid → HCID 178424870, compound

HRID 1274402Notes

Reaction equation

HRID 1274402 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([CH3:27])([C:21]3[NH:22][CH:23]=[C:24]([CH3:26])[N:25]=3)[CH3:20])[CH:17]=2)[NH:12][C:11]=1[C:28]1[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([CH3:35])[CH:29]=1)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[CH3:35][C:30]1[CH:29]=[C:28]([C:11]2[NH:12][C:13]3[C:18]([C:10]=2[CH2:9][CH2:8][NH2:7])=[CH:17][C:16]([C:19]([CH3:27])([C:21]2[NH:22][CH:23]=[C:24]([CH3:26])[N:25]=2)[CH3:20])=[CH:15][CH:14]=3)[CH:33]=[C:32]([CH3:34])[CH:31]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 178424872HCID 178424872, compound

Product 1

HCID 178424870HCID 178424870, compoundYield 70.6%

Procedure

To a solution of (2-{2-(3,5-dimethylphenyl)-5-[1-methyl-1-(4-methyl-1H-imidazol-2-yl)ethyl]-1H-indol-3-yl}ethyl)carbamic acid tert-butyl ester (353 mg in 8 mL methylene chloride) at 0° C. was added 0.56 mL anisole followed by 2.5 mL trifluoroacetic acid and the mixture stirred at room temperature. After 2 hours, the mixture was concentrated in vacuo and the residual acid removed by azeotrope with toluene. The residue was solvated in methylene chloride and washed sequentially with 0.5N sodium hydroxide and brine. Purification of the concentrate by preparative tlc on silica gel (methylene chloride:methanol:ammonium hydroxide, 80:20:0.25) to give the title compound (198 mg).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residual acid removed by azeotrope with toluene
  3. washwashed sequentially with 0.5N sodium hydroxide and brine
  4. customPurification of the
  5. concentrationconcentrate by preparative tlc on silica gel (methylene chloride:methanol:ammonium hydroxide, 80:20:0.25)

Sources & evidence

ORD record
ord-db314661266846429c7f4c7898fa119c
Source dataset
uspto-grants-2000_12
Patent number
US06156767

Reaction notes

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