Hydrochloric Acid → HCID 178450089, compound

HRID 74438Notes

Reaction equation

HRID 74438 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20](S(C2C=CC(C)=CC=2)(=O)=O)[C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:23][CH:22]=2)=[O:18].[OH-].[Na+].Cl>O1CCOCC1>[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:23][CH:22]=2)=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178450039HCID 178450039, compound

Product 1

HCID 178450089HCID 178450089, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture consisting of [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[5-butoxy-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-methanone (70 mg), dioxane (3 ml), and an aqueous solution of 5 M sodium hydroxide (300 μl) was stirred under reflux for two hours. The reaction mixture was cooled in an ice bath, and acidified with an aqueous solution of 5 M hydrochloric acid. The solvent was distilled off under reduced pressure. Water was added to the residue obtained by concentration under reduced pressure. The solid was collected by filtration, washed with water, and dried to give [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(5-butoxy-1H-indol-2-yl)-methanone (35 mg, 65%).

Workup

  1. temperatureunder reflux for two hours
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionWater was added to the residue
  5. customobtained by concentration under reduced pressure
  6. filtrationThe solid was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-d92771c5c8c74e7f8a494be009c96593
Source dataset
uspto-grants-2014_09
Patent number
US08829199B2

Reaction notes

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