HCID 69697079, compound → HCID 69697996, compound

HRID 412621Notes

Reaction equation

HRID 412621 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]([CH2:22][CH2:23][C:24](=O)[NH:25][C:26]2[CH:31]=[C:30]([C:32]#[N:33])[CH:29]=[CH:28][C:27]=2[NH:34][CH2:35][C:36](=[O:44])[NH:37][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1>C(O)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]([CH2:22][CH2:23][C:24]2[N:34]([CH2:35][C:36](=[O:44])[NH:37][CH:38]3[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]3)[C:27]3[CH:28]=[CH:29][C:30]([C:32]#[N:33])=[CH:31][C:26]=3[N:25]=2)([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 1

HCID 69697079HCID 69697079, compound

Product 1

HCID 69697996HCID 69697996, compoundYield 137.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-[2-[5-cyano-2-(cyclohexylcarbamoylmethylamino)-phenylcarbamoyl]ethyl]-4-ethoxycarbonylpiperidine-1-carboxylic acid benzyl ester (300 mg) in acetic acid (10 ml) was stirred at 100° C. for 24 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and washed with aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:3) and dried under reduced pressure to give the title compound (200 mg).

Workup

  1. customAfter completion of the reaction
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washwashed with aqueous sodium hydrogencarbonate solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:3)
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-ff1727f01ecc457e997c41d3d39cf63a
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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