Hydrochloric Acid → HCID 86670483, compound

HRID 68978Notes

Reaction equation

HRID 68978 reaction equation
Cl.C([O:4][CH:5](OCC)[C:6]1[CH:45]=[CH:44][C:9]([CH2:10][N:11]([CH2:25][C:26]2[CH:43]=[CH:42][C:29]3[N:30]([CH2:40][CH3:41])[C:31](=[O:39])[C:32]([CH3:38])([CH3:37])[C:33](=[O:36])[N:34]([CH3:35])[C:28]=3[CH:27]=2)[CH2:12][CH2:13][N:14]2[CH:19]=[CH:18][C:17]3[O:20][C:21]([CH3:23])=[CH:22][C:16]=3[C:15]2=[O:24])=[CH:8][CH:7]=1)C.[OH-].[Na+]>C1COCC1>[CH2:40]([N:30]1[C:31](=[O:39])[C:32]([CH3:38])([CH3:37])[C:33](=[O:36])[N:34]([CH3:35])[C:28]2[CH:27]=[C:26]([CH2:25][N:11]([CH2:10][C:9]3[CH:44]=[CH:45][C:6]([CH:5]=[O:4])=[CH:7][CH:8]=3)[CH2:12][CH2:13][N:14]3[CH:19]=[CH:18][C:17]4[O:20][C:21]([CH3:23])=[CH:22][C:16]=4[C:15]3=[O:24])[CH:43]=[CH:42][C:29]1=2)[CH3:41]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70656788HCID 70656788, compound

Product 1

HCID 86670483HCID 86670483, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2N-hydrochloric acid (5 ml) was added to an THF solution (5 ml) of 7-({N-(4-diethoxymethylbenzyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)-1-ethyl-3,3,5-trimethyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione (0.52 g), and the mixture was stirred at room temperature for 1 hour. 2N-Sodium hydroxide solution (5 ml) was added to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was dried with sodium sulfate, and was condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate). The purified product was condensed under reduced pressure. The residue was recrystallized from ethyl acetate and ether, and dried to give the title compound (0.35 g) as a white powder.

Workup

  1. extractionfollowed by extraction
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. customcondensed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  5. customcondensed under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate and ether
  7. customdried

Sources & evidence

ORD record
ord-ee093c1abe204fba9c9b05af3805ab82
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

Loading…