Potassium Iodide → HCID 135961835, compound

HRID 2234116Notes

Reaction equation

HRID 2234116 reaction equation
C[O:2][C:3]1[N:8]=[N:7][C:6]([C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([OH:16])=[C:11]([CH3:17])[CH:10]=2)=[CH:5][C:4]=1[C:18]1[NH:19][C:20]2[C:25]([C:26]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[CH:24][CH:23]=[C:22]([CH2:33][N:34]1[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]1)[CH:21]=2.C[Si](Cl)(C)C.[I-].[K+]>C(#N)C>[OH:16][C:12]1[C:11]([CH3:17])=[CH:10][C:9]([C:6]2[CH:5]=[C:4]([C:18]3[NH:19][C:20]4[C:25]([C:26]=3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:24][CH:23]=[C:22]([CH2:33][N:34]3[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]3)[CH:21]=4)[C:3](=[O:2])[NH:8][N:7]=2)=[CH:14][C:13]=1[CH3:15]

Participants

5

Reactant 3

HCID 4875Potassium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 136367319HCID 136367319, compound

Product 1

HCID 135961835HCID 135961835, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

48 mg 4-{6-Methoxy-5-[6-(4-methyl-piperazin-1-ylmethyl)-3-phenyl-1H-indol-2-yl]-pyridazin-3-yl}-2,6-dimethyl-phenol are dissolved in 1.2 mL acetonitrile. 34 □L TMSCl and 45 mg potassium iodide are added. The reaction mixture is heated to reflux for 3 hours. Again 34 □L TMSCl and 45 mg potassium iodide are added and the reaction mixture stirred for an additional 2 hours. Purification by HPLC affords 16 mg (34%) 6-(4-hydroxy-3,5-dimethyl-phenyl)-4-[6-(4-methyl-piperazin-1-yl-methyl)-3-phenyl-1H-indol-2-yl]-2H-pyridazin-3-one as its trifluoroacetate salt.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 3 hours
  3. customPurification by HPLC

Sources & evidence

ORD record
ord-833ebff8331747028f5f4cd032f47686
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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