Acetone → N-[3-({N-(1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)pyridin-2-ylmethyl]formamide

HRID 1504146Notes

Reaction equation

HRID 1504146 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]([CH2:19][N:20]([CH2:34][C:35]3[C:36]([C:41]#[N:42])=[N:37][CH:38]=[CH:39][CH:40]=3)[CH2:21][CH2:22][N:23]3[CH:28]=[CH:27][C:26]4[O:29][C:30]([CH3:32])=[CH:31][C:25]=4[C:24]3=[O:33])[CH:17]=[CH:18][C:4]1=2)[CH3:2].C[C:44](C)=[O:45]>[Ni].C(O)=O>[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]([CH2:19][N:20]([CH2:34][C:35]3[C:36]([CH2:41][NH:42][CH:44]=[O:45])=[N:37][CH:38]=[CH:39][CH:40]=3)[CH2:21][CH2:22][N:23]3[CH:28]=[CH:27][C:26]4[O:29][C:30]([CH3:32])=[CH:31][C:25]=4[C:24]3=[O:33])[CH:17]=[CH:18][C:4]1=2)[CH3:2]

Participants

5

Reactant 2

HCID 180AcetoneHCID 706571733-({N-(1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)pyridine-2-carbonitrile

Product 1

HCID 86670481N-[3-({N-(1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)pyridin-2-ylmethyl]formamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 284Formic AcidSolvent

Conditions

Temperature
60 °C

Procedure

3-({N-(1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)pyridine-2-carbonitrile(0.40 g) and Raney nickel(1.2 g) were suspended in formic acid(8 ml), and the mixture was stirred at 60° C. for 3 hours. The reaction mixture was filtered to remove insoluble matter, and the filtrate was condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate: methanol=75:25→80:20). The purified product was condensed under reduced pressure. Acetone and ether were added to the residue. The precipitated insoluble matter was separated, washed with ether, and dried to give the title compound(33 mg) as a pale brown white amorphous.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove insoluble matter
  3. customcondensed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate: methanol=75:25→80:20)
  5. customcondensed under reduced pressure
  6. customThe precipitated insoluble matter was separated
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-2e84bcf6f4024f84bf8a9905f7524cf5
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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