Water → HCID 59925509, compound

HRID 2301402Notes

Reaction equation

HRID 2301402 reaction equation
[CH2:1]([O:3][CH:4]([O:31][CH2:32][CH3:33])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:26][C:27]([OH:29])=O)([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[O:17])[C:7]1=[O:30])[CH3:2].[NH2:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][OH:40])=[CH:37][CH:36]=1.Cl.C(N=C=NCCCN(C)C)C.O>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:3][CH:4]([O:31][CH2:32][CH3:33])[CH2:5][N:6]1[C:14]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@:8]([CH2:26][C:27]([NH:34][C:35]2[CH:42]=[CH:41][C:38]([CH2:39][OH:40])=[CH:37][CH:36]=2)=[O:29])([NH:15][C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)=[O:17])[C:7]1=[O:30])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 693314-Aminobenzyl alcoholHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15458211HCID 15458211, compound

Product 1

HCID 59925509HCID 59925509, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
22.5 °C

Procedure

(+)-1-(2,2-diethoxyethyl)-3-hydroxycarbonylmethyl-3-(N′-(4-methylphenyl)ureido)indolin-2-one (compound described in “Example 174(1)” of Japanese Patent Application Laid-Open No. 7-48349, 300 mg) was dissolved in acetonitrile (10 mL), and after adding p-aminobenzylalcohol (100 mg) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (151 mg) in that order, the mixture was stirred at 15-30° C. for 18 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, the organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off. The resulting reaction mixture was purified by column chromatography to obtain 324 mg of the title compound (yield: 88%).

Workup

  1. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  2. distillationthe solvent was distilled off
  3. customThe resulting reaction mixture
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-1393d0d71ebb47f18e9c6889d990e777
Source dataset
uspto-grants-2002_12
Patent number
US06500854B1

Reaction notes

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