Sodium Hydroxide → 5-((4-(4-(3-(Cyclopropylmethyl)ureido)benzoyl)piperazin-1-yl)methyl)-thiophene-2-carboxylic acid

HRID 408866Notes

Reaction equation

HRID 408866 reaction equation
[CH:1]1([CH2:4][NH:5][C:6](=[O:32])[NH:7][C:8]2[CH:31]=[CH:30][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[S:25][C:24]([C:26]([O:28]C)=[O:27])=[CH:23][CH:22]=4)[CH2:16][CH2:15]3)=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([CH2:4][NH:5][C:6](=[O:32])[NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([N:14]3[CH2:15][CH2:16][N:17]([CH2:20][C:21]4[S:25][C:24]([C:26]([OH:28])=[O:27])=[CH:23][CH:22]=4)[CH2:18][CH2:19]3)=[O:13])=[CH:30][CH:31]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58055790Methyl 5-((4-(4-(3-(cyclopropylmethyl)ureido)benzoyl)piperazin-1-yl)methyl)thiophene-2-carboxylate

Product 1

HCID 666616175-((4-(4-(3-(Cyclopropylmethyl)ureido)benzoyl)piperazin-1-yl)methyl)-thiophene-2-carboxylic acidYield 58.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-((4-(4-(3-(cyclopropylmethyl)ureido)benzoyl)piperazin-1-yl)methyl)-thiophene-2-carboxylate (3.86 mmol, 1.764 g) and sodium hydroxide (3.86 mmol, 0.155 g) were combined and heated to reflux in methanol for 18 hours. The reaction mixture was concentrated at reduced pressure and the resulting residue purified by SCX column chromatography to afford the title compound (1.00 g).

Workup

  1. temperatureheated
  2. concentrationThe reaction mixture was concentrated at reduced pressure
  3. customthe resulting residue purified by SCX column chromatography

Sources & evidence

ORD record
ord-2fcfb496701149f2ba92dbe6a3097dd0
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

Loading…