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 1504224Notes

Reaction equation

HRID 1504224 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-c1c2119cc6f84a899fcd82f861fe0453
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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