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

HRID 517329

Reaction equation

HRID 517329 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-cc29a6b81db1469dabc7c771c1072f24
Source dataset
uspto-grants-2015_08
Patent number
US09115107B2

Linked notes

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