7-Chloro-1,8-naphthyridin-2-amine → HCID 13983405, compound

HRID 580486Notes

Reaction equation

HRID 580486 reaction equation
[O:1]1[CH2:6][CH2:5][S:4][CH:3]=[C:2]1[C:7]([OH:9])=O.[NH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[N:14][C:15]([Cl:21])=[CH:16][CH:17]=2)[N:12]=1>O>[Cl:21][C:15]1[N:14]=[C:13]2[C:18]([CH:19]=[CH:20][C:11]([NH:10][C:7]([C:2]3[O:1][CH2:6][CH2:5][S:4][CH:3]=3)=[O:9])=[N:12]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 851997-Chloro-1,8-naphthyridin-2-amineHCID 64232621,4-Oxathiin-2-carboxylicacid, 5,6-dihydro-

Product 1

HCID 13983405HCID 13983405, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure is similar to that described in Example 2, but starting with 5,6-dihydro-1,4-oxathiin-2-carboxylic acid (7.3 g), N,N'-carbonyldiimidazole (9.7 g) and 2-amino-7-chloro-1,8-naphthyridine (7.2 g). The product obtained by precipitation in water is purified by recrystallization in dimethylformamide (60 cc). N-(7-Chloro-1,8-naphthyridin-2-yl)-5,6-dihydro-1,4-oxathiin-2-carboxamide (5.9 g), m.p. 270° C., is thereby obtained.

Workup

  1. customis purified by recrystallization in dimethylformamide (60 cc)

Sources & evidence

ORD record
ord-bb6dbf27525b4ccdb7681ca6268312fb
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Reaction notes

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