HCID 86753449, compound → HCID 22100896, compound

HRID 1458346Notes

Reaction equation

HRID 1458346 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]([NH:19][C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[CH:17]=2)[NH:12][C:11]=1[C:25]1[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[CH:26]=1)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[NH2:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20](=[O:21])[N:22]([CH3:24])[CH3:23])[CH:17]=2)[NH:12][C:11]=1[C:25]1[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[CH:26]=1

Participants

5

Reactant 1

HCID 86753449HCID 86753449, compound

Product 1

HCID 22100896HCID 22100896, compoundYield 96.8%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

{2-[2-(3,5-dimethylphenyl)-5-(3,3-dimethylureido)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester (295 mg) was dissolved in a ternary solvent mixture comprising methylene chloride (6 mL), trifluoroacetic acid (2 mL) and anisole (2 mL) for 2.5 h. The volatile solvent components were removed on a rotary evaporator and the residues taken up in methanol and purified on four (20×20 cm 1000μ) preparative silica gel plates and eluted with a solvent system comprising methanol and methylene chloride in the ratio (1:9 v/v). The product (222 mg) was isolated as a foamy material.

Workup

  1. customThe volatile solvent components were removed on a rotary evaporator
  2. custompurified on four (20×20 cm 1000μ) preparative silica gel plates
  3. washeluted with a solvent system comprising methanol and methylene chloride in the ratio (1:9 v/v)

Sources & evidence

ORD record
ord-38b1c67109d445ecb7c1d73922e9ba1f
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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