Benzenecarboximidamide, 4-hydroxy-, hydrochloride (1:1) → 3-[5-(4-Amidinophenoxycarbonyl)thiophen-2-yl]-2-methylpropenoic acid tert-butyl ester

HRID 332598

Reaction equation

HRID 332598 reaction equation
[C:1]([O:5][C:6]([C:8]([CH3:18])=[CH:9][C:10]1[S:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.O[C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[NH:26])=[CH:23][CH:22]=1.CCN=C=NCCCN(C)C.Cl>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:7])[C:8]([CH3:18])=[CH:9][C:10]1[S:14][C:13]([C:15]([O:17][C:21]2[CH:29]=[CH:28][C:24]([C:25](=[NH:26])[NH2:27])=[CH:23][CH:22]=2)=[O:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 217124Benzenecarboximidamide, 4-hydroxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 774784945-(2-(tert-Butoxycarbonyl)-1-propenyl)-2-thiophenecarboxylic acid

Product 1

HCID 866733173-[5-(4-Amidinophenoxycarbonyl)thiophen-2-yl]-2-methylpropenoic acid tert-butyl esterYield 86.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-(2-(tert-Butoxycarbonyl)-1-propenyl)-2-thiophenecarboxylic acid (0.51 g, 1.89 mmol) and 4-hydroxybenzamidine hydrochloride (0.33 g, 1.89 mmol) were dissolved in pyridine (10 mL), WSC hydrochloride (0.54 g, 2.8 mmol) was added, and the mixture was stirred overnight. The mixture was purified by high performance liquid chromatography and freeze-dried to give the title compound (0.63 g).

Workup

  1. customThe mixture was purified by high performance liquid chromatography
  2. customfreeze-dried

Sources & evidence

ORD record
ord-5e0432ef141d42db9586f1e6a148c2eb
Source dataset
uspto-grants-2014_11
Patent number
US08877805B2

Linked notes

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