HCID 15248974, compound → HCID 9800355, compound

HRID 1532626Notes

Reaction equation

HRID 1532626 reaction equation
[CH2:1]([N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:14])[CH:2]1[O:4][CH2:3]1.[NH:15]1[CH:20]=[CH:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1>>[NH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]([C:18]2[CH2:19][CH2:20][N:15]([CH2:3][CH:2]([OH:4])[CH2:1][N:5]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[N:7]=[C:6]3[CH3:14])[CH2:16][CH:17]=2)=[CH:22]1

Participants

3

Reactant 2

HCID 15248974HCID 15248974, compoundHCID 21184334HCID 21184334, compound

Product 1

HCID 9800355HCID 9800355, compoundYield 9%

Procedure

A methanolic solution of 1-N-glycidyl-2-methylbenzimidazole (0.64 g, 3.4 mmole) from example 7 and 3-(4-tetrahydropyridinyl)indole (0.67 g, 3.4 mmole) was refluxed under nitrogen for 24 hours. The reaction mixture was concentrated in vacuo and the product purified by flash silica gel chromatography (10% methanol in ethyl acetate) to afford the titled compound as a pale yellow colored solid (0.11 g, 9% yield). Treatment with a 0.25M ethanolic solution of fumaric acid (0.5 equivalents) gave the required product as a yellow colored solid. The product was recrystallized from ethanol.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe product purified by flash silica gel chromatography (10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-5effe5aea33d40f4aa3090e46821d178
Source dataset
uspto-grants-2001_03
Patent number
US06204274B1

Reaction notes

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