HCID 21435019, compound → HCID 178466020, compound

HRID 2398244Notes

Reaction equation

HRID 2398244 reaction equation
[CH2:1]([O:3][C:4]1[N:13]=[C:12]2[C:7]([C:8](=[O:19])[C:9]([C:16]([OH:18])=O)=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:6][CH:5]=1)[CH3:2].[NH2:20][C:21]1[NH:25][N:24]=[N:23][N:22]=1>CN(C)C=O>[CH2:1]([O:3][C:4]1[N:13]=[C:12]2[C:7]([C:8](=[O:19])[C:9]([C:16]([NH:20][C:21]3[NH:25][N:24]=[N:23][N:22]=3)=[O:18])=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 21435019HCID 21435019, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178466020HCID 178466020, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Ethoxy-1-ethyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (2.0 g) and N,N'-carbonyldiimidazole (1.85 g) in dimethylformamide (40 ml) were stirred and heated to 100° for 7 hours. 5-Amino-1H-tetrazole (1.3 g) was added and the mixture heated at 100° for 1 hour and cooled. The solid was collected and dissolved in hot aqueous dimethylaminoethanol (20 ml, 5%). The hot solution was acidified with hydrochloric acid and the solid was filtered off, washed with water and dried, m.p. above 307° (d), (61%).

Workup

  1. temperatureheated to 100° for 7 hours
  2. temperaturethe mixture heated at 100° for 1 hour
  3. temperaturecooled
  4. customThe solid was collected
  5. dissolutiondissolved in hot aqueous dimethylaminoethanol (20 ml, 5%)
  6. filtrationthe solid was filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-ba062c252e9b41e991a4d14a5ff0d6b0
Source dataset
uspto-grants-1977_05
Patent number
US04024255

Reaction notes

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