Ethyl Acetate → 4-(1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane

HRID 637074Notes

Reaction equation

HRID 637074 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2Cl)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[NH:22]1[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.N12CCCN=C1CCCCC2.C(OCC)(=O)C>N1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[N:22]2[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 68163Hexahydro-1,4-diazepineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 184649721-(5-(ethoxycarbonyl)fur-2-ylmethyl)-2-chloro-1H-benzimidazole

Product 1

HCID 184646564-(1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Combine 1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-2-chloro-1H-benzimidazole (10 mmol), [1,4]diazepane (10 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (1.8 mL) in pyridine (20 mL). Heat to reflux. After 2 days, evaporate in vacuo to give a residue. Combine the residue and ethyl acetate. Extract with water and brine. Dry the the organic layer over Na2SO4, filter, and evaporate in vacuo to give 4-(1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane.

Workup

  1. temperatureHeat to reflux
  2. customevaporate in vacuo
  3. customto give a residue
  4. extractionExtract with water and brine
  5. dry with materialDry the the organic layer over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-e63e8fa788a24b1cb9b7713dfe06df7b
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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