HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → (1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine

HRID 323338
Notes
Print preview

Reaction equation

HRID 323338 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:29][C:30]1[O:34][C:33]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:32][CH:31]=1.O>CN(C)C=O.CC(C)=O.ClCCl>[CH2:38]([O:37][C:35]([C:33]1[O:34][C:30]([CH2:29][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[C:2]2[NH:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:31][CH:32]=1)=[O:36])[CH3:39]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylateHCID 30184551-Piperidinecarboxylic acid, 4-(1H-benzimidazol-2-ylamino)-, ethyl ester

Product 1

HCID 22009363(1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

Combine (1H-benzimidazol-2-yl)(1-ethoxycarbonyl-piperidin-4-yl)amine (10.94 g, 37.9 mmol), sodium carbonate (6.03 g, 57 mmol), and ethyl 5-chloromethyl-2-furoate (12.88 g, 68.3 mmol) in dimethylformamide (115 mL). Heat at about 70° C. After 18 hours, cool the reaction mixture and pour into water. Extract four times with 2/1 ethyl acetate/toluene. Combine the organic layers and extract with brine. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 20% acetone/dichloromethane. Combine the product containing fractions and evaporate in in vacuo to give a residue. Triturate the residue with diethyl ether to give a solid. Collect the solid by filtration, rinse with diethyl ether, and dry to give (1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine. Recrystallization of an analytical sample (0.3 g) from ethyl acetate/hexane (about 1 mL/4 mL) gives (1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine: mp; 133-135° C. Elemental Analysis calculated for C23H28N4O5: C 62.71; H 6.41; N 12.72; Found: C 62.69; H 6.29; N 12.66.

Workup

  1. temperaturecool the reaction mixture
  2. extractionExtract four times with 2/1 ethyl acetate/toluene
  3. extractionextract with brine
  4. dry with materialDry the combined organic layers over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto obtain a residue
  8. additioncontaining fractions
  9. customevaporate in in vacuo
  10. customto give a residue
  11. customTriturate the residue with diethyl ether
  12. customto give a solid
  13. customCollect the solid
  14. filtrationby filtration
  15. washrinse with diethyl ether
  16. customdry

Sources & evidence

ORD record
ord-31cc1519bbd24590a843f7194a9ca853
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211199B1

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes