Triethylamine → N-(sec-Butyl)-N-methyl-1-(thiophen-2-yl)isoquinoline-3-carboxamide

HRID 615397Notes

Reaction equation

HRID 615397 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([C:16]([OH:18])=O)[N:7]=1.C(N(CC)CC)C.ClC(OCC)=O.[CH3:32][NH:33][CH:34]([CH2:36][CH3:37])[CH3:35]>C(Cl)(Cl)Cl>[CH3:32][N:33]([CH:34]([CH3:35])[CH2:36][CH3:37])[C:16]([C:8]1[N:7]=[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 111026N-Methyl-2-butanamineHCID 132723951-(Thiophen-2-yl)isoquinoline-3-carboxylic acid

Product 1

HCID 13272380N-(sec-Butyl)-N-methyl-1-(thiophen-2-yl)isoquinoline-3-carboxamideYield 65.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Operations are carried out as for Example 7, starting from 3 g of 1-(2-thienyl) isoquinoline 3-carboxylic acid, 1.73 g of triethylamine, 1.86 g of ethyl chloroformate and 1.69 g of N-methyl 2-butanamine in 150 ml of chloroform. 2.5 g of N-methyl N-(1-methyl propyl) 1-(2-thienyl) isoquinoline 3-carboxamide, melting at 146° C. are obtained.

Sources & evidence

ORD record
ord-22a6cf91fccc4bd68a54fea81b3b8254
Source dataset
uspto-grants-1985_02
Patent number
US04499094

Reaction notes

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