Trifluoroacetic acid → HCID 67666689, compound

HRID 1458374Notes

Reaction equation

HRID 1458374 reaction equation
C(OC(=O)[N:7]([CH2:18][CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:29](=[O:35])[N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])[CH:27]=2)[NH:22][C:21]=1[C:36]1[CH:41]=[C:40]([Cl:42])[CH:39]=[C:38]([Cl:43])[CH:37]=1)[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[CH2:33]([N:30]([CH2:31][CH3:32])[C:29]([C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([C:36]1[CH:41]=[C:40]([Cl:42])[CH:39]=[C:38]([Cl:43])[CH:37]=1)=[C:20]2[CH2:19][CH2:18][NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:35])[CH3:34]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 7519AnisoleHCID 86753452HCID 86753452, compound

Product 1

HCID 67666689HCID 67666689, compoundYield 71.6%

Conditions

Temperature
0 °C

Procedure

To a solution of {2-[2-(3,5-dichlorophenyl)-5-diethylcarbamoyl-1H-indol-3-yl]ethyl}-(4-pyridin-3-yl-butyl)carbamic acid tert-butyl ester (63 mg in 3 mL methylene chloride) at 0° C. was added 0.15 mL anisole followed by 0.76 miL trifluoroacetic acid and the mixture stirred at 0° C. After 1.5 hours, an additional charge of 0.5 mL trifluoroacetic acid was added and stirring continued for another hour at which time the mixture was concentrated in vacuo and the residual acid removed by azeotrope with toluene. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:6.5:1) gave the title compound (38 mg). m/e=537 (M)

Workup

  1. additionwas added
  2. stirringstirring
  3. waitcontinued for another hour at which time
  4. concentrationthe mixture was concentrated in vacuo
  5. customthe residual acid removed by azeotrope with toluene
  6. customPurification of the
  7. concentrationconcentrate by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:6.5:1)

Sources & evidence

ORD record
ord-130e1225291445f495710ad89daa920d
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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