Ammonia → HCID 19093751, compound

HRID 487393Notes

Reaction equation

HRID 487393 reaction equation
[NH3:1].[CH2:2]([C:4]1[N:13]=[C:12]([CH2:14][CH3:15])[CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([C:54]([O:56]CC)=O)[C:8](=[O:53])[N:9]2[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[N:30]=[N:31][N:32]([C:34]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:33]=2)=[CH:19][CH:18]=1)[CH3:3]>CO.ClCCl>[CH2:2]([C:4]1[N:13]=[C:12]([CH2:14][CH3:15])[CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([C:54]([NH2:1])=[O:56])[C:8](=[O:53])[N:9]2[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[N:30]=[N:31][N:32]([C:34]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[N:33]=2)=[CH:21][CH:22]=1)[CH3:3]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 19093674HCID 19093674, compound

Product 1

HCID 19093751HCID 19093751, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Concentrated aqueous ammonia solution (d 0.88) was added dropwise to a solution of ethyl 5,7-diethyl-2-oxo-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,2-dihydro-1,6-naphthyridine-3-carboxylate (600 mg) in a mixture of methanol (7 ml) and dichloromethane (1.5 ml) until the solution became cloudy. Dichloromethane (2 ml) was added to give a clear solution and the mixture was stirred for 3 days. Volatile material was then removed by evaporation to give 5,7-diethyl-2-oxo-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-biphenyl-4-yl)methyl]-1,2-dihydro-1,6-naphthyridine-3-carboxamide as a solid (500 mg), which was used without further purification or characterisation.

Workup

  1. customto give a clear solution
  2. customVolatile material was then removed by evaporation

Sources & evidence

ORD record
ord-4c450d47f30c4d9f9089df88b59de62b
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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