Dimethyl Sulfoxide → 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-carbaldehyde

HRID 68980

Reaction equation

HRID 68980 reaction equation
I(C1C=CC=CC=1C(O)=O)(=O)=O.CS(C)=O.[CH2:17]([N:19]1[C:25](=[O:26])[C:24]([CH3:28])([CH3:27])[C:23](=[O:29])[N:22]([CH3:30])[C:21]2[CH:31]=[C:32]([CH2:35][N:36]([CH2:50][C:51]3[C:52]([CH2:57][OH:58])=[N:53][CH:54]=[CH:55][CH:56]=3)[CH2:37][CH2:38][N:39]3[CH:44]=[CH:43][C:42]4[O:45][C:46]([CH3:48])=[CH:47][C:41]=4[C:40]3=[O:49])[CH:33]=[CH:34][C:20]1=2)[CH3:18]>O>[CH2:17]([N:19]1[C:25](=[O:26])[C:24]([CH3:28])([CH3:27])[C:23](=[O:29])[N:22]([CH3:30])[C:21]2[CH:31]=[C:32]([CH2:35][N:36]([CH2:50][C:51]3[C:52]([CH:57]=[O:58])=[N:53][CH:54]=[CH:55][CH:56]=3)[CH2:37][CH2:38][N:39]3[CH:44]=[CH:43][C:42]4[O:45][C:46]([CH3:48])=[CH:47][C:41]=4[C:40]3=[O:49])[CH:33]=[CH:34][C:20]1=2)[CH3:18]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 1087942-Iodoxybenzoic acidHCID 669612451-Ethyl-7-({N-(2-hydroxymethylpyridin-3-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 888768503-({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-carbaldehydeYield 60.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-iodoxybenzoic acid (IBX, 0.235 g) was added to the dimethyl sulfoxide suspension (10 mL) of 1-ethyl-7-((N-((2-(hydroxymethyl)pyridin-3-yl)methyl)-N-(2-(2-methyl-4-oxofuro[3,2-c]pyridin-5(4H)-yl)ethyl)amino)methyl)-3,3,5-trimethyl-1H-benzo[b][1,4]diazepine-2,4(3H, 5H)-dione (0.48 g) and the mixture was stirred overnight at room temperature. Water was added to the resulting mixture and then the mixture was extracted with ethyl acetate twice. The combined organic layer was concentrated under reduced pressure, and then the residue was purified by column-chromatography (ethyl acetate:hexanes=50:50→100:0). The purified product was recrystallized from ether to afford the titled compound as ivory powder (0.29 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate twice
  2. concentrationThe combined organic layer was concentrated under reduced pressure
  3. customthe residue was purified by column-chromatography (ethyl acetate:hexanes=50:50→100:0)
  4. customThe purified product was recrystallized from ether

Sources & evidence

ORD record
ord-b3e399c4d7394693a006696ab522c08e
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Linked notes

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