Potassium Hydroxide → HCID 73865447, compound

HRID 1458339Notes

Reaction equation

HRID 1458339 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH2:20][CH2:21][NH:22][CH2:23][CH:24]=[CH:25][C:26]2[CH:38]=[CH:37][C:29]4[N:30](S(C)(=O)=O)[CH:31]=[N:32][C:28]=4[CH:27]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[K+]>>[N:30]1[C:29]2[CH:37]=[CH:38][C:26]([CH:25]=[CH:24][CH2:23][NH:22][CH2:21][CH2:20][C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][C:11]=3[C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:27][C:28]=2[NH:32][CH:31]=1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 54193132HCID 54193132, compound

Product 1

HCID 73865447HCID 73865447, compoundYield 58.6%

Procedure

To a solution of {2-[2-(3,4-dimethoxyphenyl)-1H-indol-3-yl]-ethyl}-[3-(1-methanesulfonyl-1H-benzoimidazol-5-yl)-allyl]amine (24 mg in 1.5 mL methanol) at 0° C. was added 0.225 niL of a 2N solution of potassium hydroxide and the mixture allowed to warm to room temperature. After 1.5 hours, the reaction was quenched by the addition of 0.30 mL of 1N hydrochloric acid, concentrated in vacuo and purified by flash chromatography on silica gel (methylene chloride:methanol, 88:12) to give the title compound (12 mg). m/e =453 (M+H)

Workup

  1. customthe reaction was quenched by the addition of 0.30 mL of 1N hydrochloric acid
  2. concentrationconcentrated in vacuo
  3. custompurified by flash chromatography on silica gel (methylene chloride:methanol, 88:12)

Sources & evidence

ORD record
ord-95c92a1080d747118ea9be90407b8ab1
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

Loading…