N-Methylpropylamine → HCID 19867683, compound

HRID 1199057Notes

Reaction equation

HRID 1199057 reaction equation
[CH3:1][O:2][C:3]1[N:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([N:13]3[C:21](=[O:22])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]3[O:23][CH2:24][C:25]([OH:27])=O)=[N:10]2)=[CH:5][CH:4]=1.[CH3:28][NH:29][CH2:30][CH2:31][CH3:32]>CN(C)C=O>[CH3:1][O:2][C:3]1[N:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([N:13]3[C:21](=[O:22])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]3[O:23][CH2:24][C:25]([N:29]([CH3:28])[CH2:30][CH2:31][CH3:32])=[O:27])=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 12315N-MethylpropylamineHCID 19867644HCID 19867644, compound

Product 1

HCID 19867683HCID 19867683, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure is as in Example 44, but starting with [2-(7-methoxy-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyloxy]acetic acid (3.1 g) in anhydrous dimethylformamide (70 cc), N,'-carbonyldiimidazole (1.4 g) and N-methylpropylamine (0.6 g). After recrystallization in ethanol, [2-(7-methoxy-1,8-naphthyridin-2yl)-3-oxo1 -isoindolinyloxy]-N-methyl-N-propylacetamide (2.7 g), m.p. 160° C., is obtained.

Workup

  1. customAfter recrystallization in ethanol

Sources & evidence

ORD record
ord-0a0d259cd4aa4834b41233761e02ae75
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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