3-(4-Aminophenyl)propionic acid → HCID 178426936, compound

HRID 640937Notes

Reaction equation

HRID 640937 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:30].[NH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][C:40]([OH:42])=[O:41])=[CH:34][CH:33]=1>C1COCC1>[CH3:29][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:8]2[CH:7]=[C:6]3[C:11]([C:3](=[CH:2][NH:31][C:32]4[CH:33]=[CH:34][C:35]([CH2:38][CH2:39][C:40]([OH:42])=[O:41])=[CH:36][CH:37]=4)[C:4](=[O:30])[NH:5]3)=[CH:10][CH:9]=2)=[O:13])=[O:22])=[CH:27][C:26]([CH3:28])=[N:25]1

Participants

4

Reactant 2

HCID 754513-(4-Aminophenyl)propionic acidHCID 178426964HCID 178426964, compound

Product 1

HCID 178426936HCID 178426936, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 60, 100 mg, 0.249 mmol) and THF (2 mL). To the resulting solution was added 3-(4-Amino-phenyl)-propionic acid (45.2 mg, 0.274 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and concentrated in vacuo. The resulting residue was redissolved into EtOAc. Hexanes were added to the EtOAc solution causing a precipitate to form. The solid precipitate that formed was washed with ˜1 mL of i-prOH yielding 15.4% (0.021 g, 0.038 mmol) of the title compound.

Workup

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resulting residue was redissolved into EtOAc
  5. additionHexanes were added to the EtOAc solution
  6. customto form
  7. customThe solid precipitate that formed

Sources & evidence

ORD record
ord-39eb54ea259545e8853915b3799248c5
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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