Cyclopentanol → HCID 15485215, compound

HRID 1586461Notes

Reaction equation

HRID 1586461 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][NH:13][C:14]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][N:17]=2)=[O:15])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[CH:25]1(O)[CH2:29][CH2:28][CH2:27][CH2:26]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][NH:13][C:14]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[N:17]=2)=[O:15])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15485213HCID 15485213, compound

Product 1

HCID 15485215HCID 15485215, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[2-(4-n-butyl-1-piperazinyl)-ethyl]-1H-indazole-3-carboxamide (0.42 g) obtained in Example 10 in THF (10 ml) were successively added cyclopentanol (0.16 g), triphenylphosphine (0.41 g) and diethyl azodicarboxylate (0.36 g) under ice-cooling, and then the mixture was stirred at room temperature for 22 hours. The residue obtained by concentration of the reaction solution was purified by silica gel column chromatography (methylene chloride:ethyl acetate=1:1-chloroform:methanol:aqueous ammonia=10:1:0.05) to give a fraction (0.47 g) containing the title compound. This fraction was separated by thin-layer chromatography on silica gel (chloroform:methanol:aqueous ammonia=10:1:0.1) to give the title compound (0.36 g) as a pale yellow oily substance. Yield=71%.

Workup

  1. temperaturecooling
  2. customThe residue obtained by concentration of the reaction solution
  3. customwas purified by silica gel column chromatography (methylene chloride:ethyl acetate=1:1-chloroform:methanol:aqueous ammonia=10:1:0.05)
  4. customto give a fraction (0.47 g)

Sources & evidence

ORD record
ord-3a3b94276f1845c7b47c21b826ed8e26
Source dataset
uspto-grants-1999_08
Patent number
US05945434

Reaction notes

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