1-(2-Thienyl)-1-aminoethane → 5-(1-Thiophen-2-yl-ethylcarbamoyl)-thiophene-2-carboxylic acid methyl ester

HRID 11431Notes

Reaction equation

HRID 11431 reaction equation
[S:1]1[C:5]([C:6]([O-:8])=O)=[CH:4][CH:3]=[C:2]1[C:9]([O:11][CH3:12])=[O:10].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[S:36]1[CH:40]=[CH:39][CH:38]=[C:37]1[CH:41]([NH2:43])[CH3:42]>C(Cl)Cl>[CH3:12][O:11][C:9]([C:2]1[S:1][C:5]([C:6](=[O:8])[NH:43][CH:41]([C:37]2[S:36][CH:40]=[CH:39][CH:38]=2)[CH3:42])=[CH:4][CH:3]=1)=[O:10]

Participants

6

Reactant 4

HCID 2382331-(2-Thienyl)-1-aminoethaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6946556HCID 6946556, compound

Product 1

HCID 471436895-(1-Thiophen-2-yl-ethylcarbamoyl)-thiophene-2-carboxylic acid methyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 500 mg (2.7 mmol) of methyl thiophen-2,5-dicarboxylate in CH2Cl2 (20 ml) is treated with 617 mg (4 mmol) 1-hydroxybenzotriazole hydrate and 772 mg (4 mmol) N′-(3-dimethylaminopropyl)-N-ethylcarbodiimid hydrochloride and stirring is continued at ambient temperature for 1 hour. 410 mg (3.2 mmol) of 1-thiophen-2-yl-ethylamine are added to the reaction mixture which is subsequently stirred at ambient temperature overnight. The product is isolated after acidic work-up and purification on silica gel as waxy solid in 84% yield (0.67 g).

Workup

  1. stirringis subsequently stirred at ambient temperature overnight
  2. customThe product is isolated
  3. customafter acidic work-up and purification on silica gel as waxy solid in 84% yield (0.67 g)

Sources & evidence

ORD record
ord-dd8830353a284752b61a36e101312188
Source dataset
uspto-grants-2006_08
Patent number
US07098241B2

Reaction notes

Loading…