Hydrogen chloride-ethyl acetate → 1-ethyl-3,3,5-trimethyl-7-{3-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-ylmethyl)imidazo[4,5-c]pyridin-1-yl]propoxy}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione dihydrochloride

HRID 69058Notes

Reaction equation

HRID 69058 reaction equation
O[CH:2](O)[CH2:3][N:4]1[CH:9]=[CH:8][C:7]2[O:10][C:11]([CH3:13])=[CH:12][C:6]=2[C:5]1=[O:14].[NH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[NH:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:45]=[CH:44][C:31]2[N:32]([CH2:42][CH3:43])[C:33](=[O:41])[C:34]([CH3:40])([CH3:39])[C:35](=[O:38])[N:36]([CH3:37])[C:30]=2[CH:29]=1.S([O-])(O)=O.[Na+].C(OC(=O)C)C.[ClH:57]>C(OCC)(=O)C.CN(C=O)C>[ClH:57].[ClH:57].[CH2:42]([N:32]1[C:33](=[O:41])[C:34]([CH3:40])([CH3:39])[C:35](=[O:38])[N:36]([CH3:37])[C:30]2[CH:29]=[C:28]([O:27][CH2:26][CH2:25][CH2:24][N:23]3[C:22]4[CH:21]=[CH:20][N:19]=[CH:18][C:17]=4[N:16]=[C:2]3[CH2:3][N:4]3[CH:9]=[CH:8][C:7]4[O:10][C:11]([CH3:13])=[CH:12][C:6]=4[C:5]3=[O:14])[CH:45]=[CH:44][C:31]1=2)[CH3:43]

Participants

7

Reactant 4

HCID 21866389Hydrogen chloride-ethyl acetateHCID 23665763Sodium BisulfiteHCID 669600005-(2,2-Dihydroxyethyl)-2-methyl-5H-furo[3,2-c]pyridine-4-oneHCID 669611607-[3-(3-Aminopyridin-4-ylamino)propoxy]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 706569581-ethyl-3,3,5-trimethyl-7-{3-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-ylmethyl)imidazo[4,5-c]pyridin-1-yl]propoxy}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione dihydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A DMF solution (4 ml) of 5-(2,2-dihydroxyethyl)-2-methyl-5H-furo[3,2-c]pyridine-4-one (0.20 g), 7-[3-(3-aminopyridin-4-ylamino)propoxy]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (0.37 g), and sodium hydrogensulfite (0.47 g) were heated at 180° C. for 10 minutes (microwave reactor). After the reaction liquid was condensed under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:methanol=95:5→60:40). The purified product was condensed under reduced pressure. A 4N-hydrogen chloride ethyl acetate solution was added to an ethyl acetate solution of the residue, which was stirred at room temperature. The generated insoluble matter was separated by filtration, and dried to give the title compound (0.47 g) as a white amorphous solid.

Workup

  1. customAfter the reaction liquid
  2. customcondensed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=95:5→60:40)
  4. customcondensed under reduced pressure
  5. customThe generated insoluble matter was separated by filtration
  6. customdried

Sources & evidence

ORD record
ord-6ca6c8ba3a5c4648b7bf7b70e9a63d07
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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