4-Aminophenylacetic acid → HCID 178463064, compound

HRID 640822Notes

Reaction equation

HRID 640822 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[N:24]([CH2:29][CH3:30])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])[CH:10]=2)[NH:5][C:4]1=[O:31].[NH2:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][C:40]([OH:42])=[O:41])=[CH:35][CH:34]=1>C1COCC1>[CH2:29]([N:24]1[C:23]([C:21]([NH:20][C:16]2[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=2)[C:12]([C:9]2[CH:8]=[C:7]3[C:6](=[CH:11][CH:10]=2)[NH:5][C:4](=[O:31])[C:3]3=[CH:2][NH:32][C:33]2[CH:34]=[CH:35][C:36]([CH2:39][C:40]([OH:42])=[O:41])=[CH:37][CH:38]=2)=[O:13])=[O:22])=[CH:27][C:26]([CH3:28])=[N:25]1)[CH3:30]

Participants

4

Reactant 2

HCID 145334-Aminophenylacetic acidHCID 178463068HCID 178463068, compound

Product 1

HCID 178463064HCID 178463064, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide (as prepared in Example 1, 30 mg, 0.072 mmol) and THF (1 mL). To the resulting solution was added 4-aminophenylacetic acid (16.4 mg, 0.1082 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature. Hexanes were added to the reaction mixture. The solid precipitate that formed was washed with ˜1 mL of ice cold THF yielding 42% (16.7 mg, 0.030 mmol) of the title compound.

Workup

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. customThe solid precipitate that formed

Sources & evidence

ORD record
ord-8227311db6d943ff9b8eadc2a79b18f4
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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