HCID 18377335, compound → HCID 18377398, compound

HRID 2301115Notes

Reaction equation

HRID 2301115 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([C:17](=[O:19])[NH2:18])=[CH:16][C:10]=2[CH2:9]1)=O)(C)(C)C>CO.Cl>[C:17]([C:15]1[S:14][C:11]2[CH2:12][CH2:13][NH:8][CH2:9][C:10]=2[CH:16]=1)(=[O:19])[NH2:18]

Participants

3

Reactant 1

HCID 18377335HCID 18377335, compound

Product 1

HCID 18377398HCID 18377398, compound

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

5-t-Butoxycarbonyl-2-carbamoyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (280 mg, 1.0 mmol) was dissolved in hydrochloric acid methanol solution and stirred at room temperature for 18 hours. By evaporating the solvent from the reaction solution under a reduced pressure, crude 2-carbamoyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine was obtained. This compound and triethylamine (0.56 ml, 4.0 mmol) and 2a-(4-bromobutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (290 mg, 0.95 mmol) were stirred at room temperature for 22 hours in anhydrous N,N-dimethylformamide (15 ml). The reaction solution was mixed with ethyl acetate, washed with water and saturated brine and then dried with anhydrous sodium sulfate. The solvent was removed by evaporation from the organic layer under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 170 mg (0.42 mmol, 44% in yield) of the title compound.

Workup

  1. customBy evaporating the solvent from the reaction solution under a reduced pressure

Sources & evidence

ORD record
ord-7956a837403a46af80793bc52d5ba6d0
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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