Acetic Acid → 1-[4-(2,5-Dihydro-1h-pyrrol-1-ylcarbonyl)benzyl]-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on hydrochloride

HRID 2417492Notes

Reaction equation

HRID 2417492 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][NH:7][CH2:8][C:9]([O:11]CC)=O)([O-])=O.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(N(CC)CC)C.[H][H].[N:42]1([C:47]([C:49]2[CH:56]=[CH:55][C:52]([CH:53]=O)=[CH:51][CH:50]=2)=[O:48])[CH2:46][CH:45]=[CH:44][CH2:43]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:75]CCl>[OH-].[Na+].C(O)C.Cl.O1CCOCC1.[Pd].C(OCC)(=O)C>[ClH:75].[N:42]1([C:47]([C:49]2[CH:50]=[CH:51][C:52]([CH2:53][N:1]3[C:4]4[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=4[CH2:6][NH:7][CH2:8][C:9]3=[O:11])=[CH:55][CH:56]=2)=[O:48])[CH2:43][CH:44]=[CH:45][CH2:46]1

Participants

15

Reactant 8

HCID 176Acetic AcidHCID 6344Dichloromethane6×HCID 8471Triethylamine2×HCID 90495Di-tert-butyl dicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 13236074Ethyl (2-nitrobenzyl)aminoacetateHCID 226325974-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benz-aldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 226323551-[4-(2,5-Dihydro-1h-pyrrol-1-ylcarbonyl)benzyl]-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on hydrochloride

Reagents, catalysts & solvents 6

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

2.0 g (8.47 mmol) of ethyl (2-nitrobenzyl)aminoacetate was dissolved in 20 ml of dichloromethane. 2.7 g (12.6 mmol) of di-t-butyl dicarbonate and 2.4 ml (16.9 mmol) of triethylamine were added to the obtained solution, and they were stirred at room temperature overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, 200 mg of 10% palladium/carbon was added to the obtained crude product and they were stirred in the presence of hydrogen at room temperature for 5 hours. The reaction solution was filtered through Celite. The solvent was evaporated and the obtained crude product was dissolved in 20 ml of dichloromethane. 670 mg (3.29 mmol) of 4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzaldehyde and 0.29 ml (5.1 mmol) of acetic acid were added to the obtained solution, and they were stirred at room temperature for 30 minutes. 1.3 g (6.3 mmol) of sodium triacetoxyborohydride was added to the reaction mixture, and they were stirred at room temperature overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in a mixture of 2 ml of 1 N sodium hydroxide and 4 ml of ethanol, and the obtained solution was stirred at room temperature for 5 hours. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 10 ml of dichloromethane. 78 mg (3.29 mmol) of 2-chloro-1,3-dimethylimidazonium chloride and 0.71 ml (5.1 mmol) of triethylamine were added to the obtained solution, and they were stirred overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 5 ml of 4N solution of hydrogen chloride in dioxane, and the obtained solution was stirred at room temperature for 3 hours. The solvent was evaporated to obtain the crude title compound.

Workup

  1. customobtained crude product and they
  2. filtrationThe reaction solution was filtered through Celite
  3. customThe solvent was evaporated
  4. customthe obtained crude product
  5. stirringwere stirred at room temperature for 30 minutes
  6. stirringwere stirred at room temperature overnight
  7. stirringthe obtained solution was stirred at room temperature for 5 hours
  8. stirringwere stirred overnight
  9. stirringthe obtained solution was stirred at room temperature for 3 hours
  10. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c55f9246d6e344898ae2d33ab16a7779
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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