2-Amino-7-phenoxy-1,8-naphthyridine → N-(7-Phenoxy-1,8-naphthyridin-2-yl)-5,6-dihydro-1,4-dithiin-2carboxamide

HRID 580485Notes

Reaction equation

HRID 580485 reaction equation
[S: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]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:17]=2)[N:12]=1>>[O:21]([C:15]1[N:14]=[C:13]2[C:18]([CH:19]=[CH:20][C:11]([NH:10][C:7]([C:2]3[S:1][CH2:6][CH2:5][S:4][CH:3]=3)=[O:9])=[N:12]2)=[CH:17][CH:16]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 137873732-Amino-7-phenoxy-1,8-naphthyridineHCID 201340095,6-Dihydro-1,4-dithiin-2-carboxylic acid

Product 1

HCID 13983404N-(7-Phenoxy-1,8-naphthyridin-2-yl)-5,6-dihydro-1,4-dithiin-2carboxamideYield 78.4%

Procedure

The procedure is similar to that described in Example 2, but starting with 5,6-dihydro-1,4-dithiin-2-carboxylic acid (10.9 g), N,N'-carbonyldiimidazole (10.9 g) and 2-amino-7-phenoxy-1,8-naphthyridine (11.9 g), and heating for 18 hours under reflux. The product obtained, after precipitation in water, washing with water and drying (18 g; m.p. approximately 240° C.), is purified by recrystallization in dimethylformamide (150 cc). N-(7-Phenoxy-1,8-naphthyridin-2-yl)-5,6-dihydro-1,4-dithiin-2carboxamide (15 g), m.p. 245° C., is thereby obtained.

Workup

  1. temperatureheating for 18 hours
  2. temperatureunder reflux
  3. customThe product obtained
  4. customafter precipitation in water
  5. washwashing with water
  6. customdrying (18 g; m.p. approximately 240° C.)
  7. customis purified by recrystallization in dimethylformamide (150 cc)

Sources & evidence

ORD record
ord-7d0084c50da441c9a890efc8158de8fb
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Reaction notes

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