2-Aminomethyl-1-ethylpyrrolidine → (+/-) 5-Carbomethoxy-N-[1-ethyl-2-pyrrolidinylmethyl]-3-methoxy-4-methylthiophene-2-carboxamide

HRID 1493360Notes

Reaction equation

HRID 1493360 reaction equation
CO[C:3]([C:5]1[S:6][C:7]([C:13]([O:15][CH3:16])=[O:14])=[C:8]([CH3:12])[C:9]=1[O:10][CH3:11])=[O:4].[NH2:17][CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH2:24][CH3:25]>C(OCC)(=O)C>[C:13]([C:7]1[S:6][C:5]([C:3]([NH:17][CH2:18][CH:19]2[CH2:23][CH2:22][CH2:21][N:20]2[CH2:24][CH3:25])=[O:4])=[C:9]([O:10][CH3:11])[C:8]=1[CH3:12])([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 19831300Dimethyl 3-methoxy-4-methyl-2,5-thiophene dicarboxylate

Product 1

HCID 21625033(+/-) 5-Carbomethoxy-N-[1-ethyl-2-pyrrolidinylmethyl]-3-methoxy-4-methylthiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The above compound was prepared by heating dimethyl-3-methoxy-4-methyl-2,5-thiophene dicarboxylate and (±)2-(aminomethyl)-1-ethyl-pyrrolidine at 170° under nitrogen atmosphere. After column chromatography, the title compound was obtained, as its fumarate salt, m.p. 155°-156° ex ethyl acetate.

Workup

  1. customThe above compound was prepared

Sources & evidence

ORD record
ord-7e0cffbfaa234ae081bd10e50964b3bc
Source dataset
uspto-grants-1991_06
Patent number
US05021449

Reaction notes

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