Potassium Hydroxide → HCID 25195906, compound

HRID 645687Notes

Reaction equation

HRID 645687 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11]3[C:12]4[CH:28]=[CH:27][N:26](S(C5C=CC(C)=CC=5)(=O)=O)[C:13]=4[N:14]=[C:15]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=4)[N:16]=3)[CH:8]=2)[CH:3]=[N:2]1.ClC1C=CC=C(C(OO)=O)C=1.[OH-:50].[K+]>CC(C)=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11]3[C:12]4[CH:28]=[CH:27][NH:26][C:13]=4[N:14]=[C:15]([NH:17][C:18]4[CH:19]=[CH:20][C:21]([S:24]([CH3:25])=[O:50])=[CH:22][CH:23]=4)[N:16]=3)[CH:8]=2)[CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57585782N4-(1H-indazol-6-yl)-N2-(4-(methylthio)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Product 1

HCID 25195906HCID 25195906, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of N4-(1H-indazol-6-yl)-N2-(4-(methylthio)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine (102 mg, 0.19 mmol) in acetone (4 mL), m-chloroperbenzoic acid (mCPBA) (70%, 34 mg, 0.14 mmol) was added. After being stirred at room temperature for 2 h, the mixture was concentrated in vacuo. The residue was dissolved in dioxane (3 mL) and aq. 1N KOH (1.5 mL, 1.5 mmol) was added. After being stirred at 70° C. for 24 h, the mixture was concentrated in vacuo. The residue was acidified with acetic acid (HOAc) (2 mL) before it was purified by HPLC to give N4-(1H-indazol-6-yl)-N2-(4-(methylsulfinyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine (21 mg), MS 404.1 (M+H) (Compound 10-2); and N4-(1H-indazol-6-yl)-N2-(4-(methylthio)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine (10 mg), MS 388.1 (M+H) (Compound 10-1).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in dioxane (3 mL)
  3. stirringAfter being stirred at 70° C. for 24 h
  4. concentrationthe mixture was concentrated in vacuo
  5. customwas purified by HPLC

Sources & evidence

ORD record
ord-124b228f071541109a732bd20fedeb7a
Source dataset
uspto-grants-2010_04
Patent number
US07705004B2

Reaction notes

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