Ethanol → HCID 9890433, compound

HRID 1005932Notes

Reaction equation

HRID 1005932 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([C:12]1[CH:30]=[CH:29][C:15]([C:16]([NH:18][CH:19]3[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][C:21]([CH3:28])([CH3:27])[CH2:20]3)=[O:17])=[CH:14][C:13]=1[O:31]CC1C=CC=CC=1)=[CH:5]2.CCO.CC#N>Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([C:12]1[CH:30]=[CH:29][C:15]([C:16]([NH:18][CH:19]3[CH2:20][C:21]([CH3:27])([CH3:28])[NH:22][C:23]([CH3:25])([CH3:26])[CH2:24]3)=[O:17])=[CH:14][C:13]=1[OH:31])=[CH:5]2

Participants

5

Reactant 3

HCID 702EthanolHCID 6342AcetonitrileHCID 9959240HCID 9959240, compound

Product 1

HCID 9890433HCID 9890433, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4-(5,6-dichloro-1H-indol-2-yl)-3-benzyloxy-N-(2,2,6,6-tetramethylpiperidin-4-yl)-benzamide (0.08 g, 0.145 mmol), prepared as described in Example 2, in 37% HCl (5 ml) and EtOH (5 ml) was refluxed for 3 h. After cooling the solvent was removed under vacuum. The resulting solid was purified by column chromatography over silica gel (CH2Cl2/MeOH/NH4OH 86:10:0.6) to yield, after trituration with CH3CN, 0.02 g (yield 39%) of the title compound as a white solid, mp>270° C.

Workup

  1. customprepared
  2. temperatureAfter cooling the solvent
  3. customwas removed under vacuum
  4. customThe resulting solid was purified by column chromatography over silica gel (CH2Cl2/MeOH/NH4OH 86:10:0.6)
  5. customto yield

Sources & evidence

ORD record
ord-59af3f080c5144a79c050b9325329007
Source dataset
uspto-grants-2004_09
Patent number
US06787550B1

Reaction notes

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