Triethylamine → HCID 178422960, compound

HRID 2398252Notes

Reaction equation

HRID 2398252 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:14])[N:12]=2)[C:7](=[O:15])[C:6]([C:16]([OH:18])=O)=[CH:5]1)([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[NH2:32][C:33]1[NH:37][N:36]=[N:35][N:34]=1>CN(C)C=O>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:14])[N:12]=2)[C:7](=[O:15])[C:6]([C:16]([NH:32][C:33]2[NH:37][N:36]=[N:35][N:34]=2)=[O:18])=[CH:5]1)([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 21435005HCID 21435005, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178422960HCID 178422960, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,4-Dihydro-1-isopropyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid (Example 3b, 0.9 g) was warmed in dimethylformamide (70 ml) and triethylamine (0.7 ml) was added. The solution was cooled to 0° and ethyl chloroformate (0.4 ml) was added and the mixture was kept for 30 minutes. 5-Amino-1H-tetrazol (3.6 g) was added and the mixture was stirred at room temperature for 18 hours and filtered. The filtrate was evaporated and the residue was crystallised from a mixture of dimethylformamide and isopropanol. The product has m.p. > 300° (d) (36%).

Workup

  1. temperatureThe solution was cooled to 0°
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthe residue was crystallised from a mixture of dimethylformamide and isopropanol

Sources & evidence

ORD record
ord-2e8fc0a772c2420e9b8b542ec6b0812e
Source dataset
uspto-grants-1977_05
Patent number
US04024255

Reaction notes

Loading…