2-(3-(methylamino)propyl)-1H-benzimidazole → HCID 68412487, compound

HRID 220293Notes

Reaction equation

HRID 220293 reaction equation
[OH:1][C@@:2]1([CH2:16][CH2:17]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:7][C@H:6]2[CH2:8][CH2:9][C@@H:3]1[CH:4]=[C:5]2[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[NH:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=[C:30]1[CH2:38][CH2:39][CH2:40][NH:41][CH3:42]>CCN(C(C)C)C(C)C>[NH:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=[C:30]1[CH2:38][CH2:39][CH2:40][N:41]([CH3:42])[CH2:17][CH2:16][C:2]1([OH:1])[CH2:7][CH:6]2[CH2:8][CH2:9][CH:3]1[CH:4]=[C:5]2[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 31454002-(3-(methylamino)propyl)-1H-benzimidazoleHCID 91466714HCID 91466714, compound

Product 1

HCID 68412487HCID 68412487, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 115 mg of rac-toluene-4-sulfonic acid (1R*,2R*,4R*)-2-(2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl ester and 55 mg of [3-(1H-benzoimidazol-2-yl)-propyl]-methyl-amine in 2 mL of DIPEA was heated to 110° C. for 30 min. The reaction mixture was cooled to rt, quenched with MeOH-water and extracted with EtOAc. The organic phase was separated, dried and evaporated and the residue was purified by CC with EtOAc-MeOH (3:1) to give 34 mg of rac-(1R*,2R*,4R*)-2-(2-{[3-(1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol as beige foam.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customquenched with MeOH-water
  3. extractionextracted with EtOAc
  4. customThe organic phase was separated
  5. customdried
  6. customevaporated
  7. customthe residue was purified by CC with EtOAc-MeOH (3:1)

Sources & evidence

ORD record
ord-31feccfc7d0b463f9a35360be79965cc
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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