HCID 18697812, compound → HCID 18697912, compound

HRID 2289567Notes

Reaction equation

HRID 2289567 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([CH2:7][N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18](=[O:32])[C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[CH:21][C:20]=3[N+:29]([O-])=O)[N:10]=[N:9]2)=[CH:5][CH:4]=1.COC1C=CC(CN2C(C(=O)C3C=CC(NC(=O)C)=CC=3[N+]([O-])=O)=C(C(OCC)=O)N=N2)=CC=1>C(OCC)(=O)C.[Pd]>[NH2:29][C:20]1[CH:21]=[C:22]([NH:25][C:26](=[O:28])[CH3:27])[CH:23]=[CH:24][C:19]=1[C:18]([C:11]1[N:10]=[N:9][N:8]([CH2:7][C:6]2[CH:33]=[CH:34][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:32]

Participants

5

Reactant 2

HCID 18697812HCID 18697812, compoundHCID 18697820HCID 18697820, compound

Product 1

HCID 18697912HCID 18697912, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The 3:1 mixture (650 mg, 1.39 mmol) of ethyl 1-(4-methoxybenzyl)-4-(4-acetylamino-2-nitrobenzoyl)-1,2,3-triazole-5-carboxylate (b-1) and ethyl 1-(4-methoxybenzyl)-5-(4-acetylamino-2-nitrobenzoyl)-1,2,3-triazole-4-carboxylate (b-2) prepared in the above step (b) was dissolved in ethyl acetate (29 ml), 10% palladium on carbon (65 mg) was added to the solution, and the mixture was stirred under a hydrogen atmosphere at room temperature for four days. The reaction mixture was filtered through Celite, the filtrate was concentrated under reduced pressure, and the resultant precipitate was collected by filtration to give a 3:1 mixture (565.5 mg, 93%) of ethyl 4-(2-amino-4-acetylaminobenzoyl)-1-(4-methoxybenzyl)-1,2,3-triazole-5-carboxylate (c-1) and ethyl 5-(2-amino-4-acetylaminobenzoyl)-1-(4-methoxybenzyl)-1,2,3-triazole-5-carboxylate (c-2).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. filtrationthe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-abcc9d6fa8154dca8b9d70d69050134d
Source dataset
uspto-grants-2000_07
Patent number
US06093714

Reaction notes

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