Potassium Hydroxide → HCID 59824914, compound

HRID 886566Notes

Reaction equation

HRID 886566 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([C:24]4([CH3:31])[NH:28][C:27](=[O:29])[NH:26][C:25]4=[O:30])[CH:21]=[CH:22][CH:23]=3)[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1.[OH-].[K+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([C:24]4([CH3:31])[NH:28][C:27](=[O:29])[NH:26][C:25]4=[O:30])[CH:21]=[CH:22][CH:23]=3)[CH:16]=2)[NH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59825101HCID 59825101, compound

Product 1

HCID 59824914HCID 59824914, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-{3-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-5-methyl-imidazolidine-2,4-dione (57 mg, 0.1 mmol) in methanol (2 mL) was added potassium hydroxide (50% w/v in water, 0.4 mL) and the resulting mixture was stirred at room temperature for 1 hour. The reaction solution was purified directly by mass-triggered reverse-phase HPLC to afford 5-{3-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-5-methyl-imidazolidine-2,4-dione as a white powder (21 mg, 51%). MS: m/z 413 (M+H+). 1H NMR (500 MHz, DMSO-d6) δ 1.72 (s, 3H), 3.85 (s, 3H), 7.05 (t, 1H), 7.15 (d, 1H), 7.31 (dt, 1H), 7.49 (d, 1H), 7.51 (t, 1H), 7.57 (dd, 1H), 7.70 (d, 1H), 7.73 (d, 1H) 7.76 (s, 1H), 8.14 (d, 1H), 8.53 (d, 1H), 8.73 (s, 1H), 10.82 (s, 1H), 11.95 (s, 1H).

Workup

  1. customThe reaction solution was purified directly by mass-triggered reverse-phase HPLC

Sources & evidence

ORD record
ord-7cb1d599a0f04306963a3facfac35fad
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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