Sodium Hydroxide → HCID 178432249, compound

HRID 513826Notes

Reaction equation

HRID 513826 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]([C:27]=1[F:28])=[CH:25][CH:24]=[CH:23][CH:22]=2)=O.[OH-].[Na+]>CS(O)(=O)=O>[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[CH2:17][C:19]1[NH:20][C:21]2[C:26]([C:27]=1[F:28])=[CH:25][CH:24]=[CH:23][CH:22]=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178427392[5-Amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[3-fluoro-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-methanone

Product 1

HCID 178432249HCID 178432249, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

[5-Amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[3-fluoro-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-methanone (25.0 mg, 0.041 mmol) was dissolved in methane sulfonic acid (0.25 ml), and stirred at room temperature for one hour. The pH of the reaction mixture was adjusted to 6 using an aqueous solution of 1 M sodium hydroxide. After extraction with ethyl acetate, the extract was dried over anhydrous sodium sulfate. The desiccant was removed by filtration. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=60/1 to 40/1) to give [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(3-fluoro-1H-indol-2-yl)-methan one was obtained as a pale yellow solid (8.7 g, with a yield of 55%).

Workup

  1. extractionAfter extraction with ethyl acetate
  2. dry with materialthe extract was dried over anhydrous sodium sulfate
  3. customThe desiccant was removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=60/1 to 40/1)

Sources & evidence

ORD record
ord-71fb16a4d88e4f498ee1f42e8a170c1e
Source dataset
uspto-grants-2015_08
Patent number
US09102692B2

Reaction notes

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