Water → HCID 23510024, compound

HRID 1882903Notes

Reaction equation

HRID 1882903 reaction equation
CO[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13]3[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:7][CH:6]=1)=[O:4].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH:35]1([NH2:41])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.O>CN(C=O)C>[CH:35]1([NH:41][C:3]([C:5]2[CH:6]=[CH:7][C:8]([C:11]3[NH:12][C:13]4[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[CH:17]=[CH:16][C:14]=4[N:15]=3)=[CH:9][CH:10]=2)=[O:4])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 962WaterHCID 7965CyclohexylamineHCID 682631,1'-CarbonyldiimidazoleHCID 160843592-[4-(Methoxycarbonyl)phenyl]-1H-benzimidazole-6-carboxylic acid

Product 1

HCID 23510024HCID 23510024, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-methoxycarbonyl-phenyl)-3H-benzoimidazole-5-carboxylic acid (5.0 g) in DMF (250 mL) and CDI (7.1 g) was stirred at RT for 3.0 hours and then treated with cyclohexyl amine (2.0 g) and refluxed for 96 hours. The reaction mixture was cooled and then poured into water (2.0 L) and stirred at RT for 16 hours. The product was filtered, washed with water and ether and then recrystallized from THF, methanol and ether. Yield 0.4 g. TLC one spot (9:1)-CH2Cl2—CH3OH.

Workup

  1. temperaturerefluxed for 96 hours
  2. temperatureThe reaction mixture was cooled
  3. stirringstirred at RT for 16 hours
  4. filtrationThe product was filtered
  5. washwashed with water and ether
  6. customrecrystallized from THF, methanol and ether

Sources & evidence

ORD record
ord-7013dfd498794b31b34643516c1d0a7c
Source dataset
uspto-grants-2004_07
Patent number
US06759425B2

Reaction notes

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