1-Ethyl-3,3,5-trimethyl-7-[3-(3-nitropyridin-4-ylamino)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione → 7-[3-(3-Aminopyridin-4-ylamino)propoxy]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 69053Notes

Reaction equation

HRID 69053 reaction equation
[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([O:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][C:25]=3[N+:30]([O-])=O)[CH:17]=[CH:18][C:4]1=2)[CH3:2]>[Pd].CO>[NH2:30][C:25]1[CH:26]=[N:27][CH:28]=[CH:29][C:24]=1[NH:23][CH2:22][CH2:21][CH2:20][O:19][C:16]1[CH:17]=[CH:18][C:4]2[N:3]([CH2:1][CH3:2])[C:9](=[O:10])[C:8]([CH3:11])([CH3:12])[C:7](=[O:13])[N:6]([CH3:14])[C:5]=2[CH:15]=1

Participants

4

Reactant 1

HCID 706570661-Ethyl-3,3,5-trimethyl-7-[3-(3-nitropyridin-4-ylamino)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 669611607-[3-(3-Aminopyridin-4-ylamino)propoxy]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 83.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (0.7 g) was added to a methanol solution (30 ml) of 1-ethyl-3,3,5-trimethyl-7-[3-(3-nitropyridin-4-ylamino)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (1.8 g). The mixture was subjected to catalytic reduction at room temperature under normal pressure. The reaction mixture was subjected to celite filtration to remove the catalyst. The filtrate was condensed under reduced pressure to give the title compound (1.4 g) as an orange amorphous solid.

Workup

  1. customwas subjected to catalytic reduction at room temperature under normal pressure
  2. filtrationThe reaction mixture was subjected to celite filtration
  3. customto remove the catalyst
  4. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-b6e8fa86abfe4b729ae99f035595b7ba
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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