Hydrochloric Acid → HCID 135961908, compound

HRID 2234124Notes

Reaction equation

HRID 2234124 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[CH:15]=2)[CH:10]=[C:9]1[C:25]1[CH:30]=[C:29]([C:31]2[CH:36]=[C:35]([CH3:37])[C:34]([OH:38])=[C:33]([CH3:39])[CH:32]=2)[N:28]=[N:27][C:26]=1[O:40]C)=O)(C)(C)C.C[Si](Cl)(C)C.[I-].[K+].Cl>C(#N)C>[OH:38][C:34]1[C:33]([CH3:39])=[CH:32][C:31]([C:29]2[CH:30]=[C:25]([C:9]3[NH:8][C:16]4[C:11]([CH:10]=3)=[CH:12][CH:13]=[C:14]([CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[CH:15]=4)[C:26](=[O:40])[NH:27][N:28]=2)=[CH:36][C:35]=1[CH3:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 6397ChlorotrimethylsilaneHCID 136367320HCID 136367320, compound

Product 1

HCID 135961908HCID 135961908, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

475 mg 2-[6-(4-Hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-6-(4-methyl-piperazin-1-ylmethyl)-indole-1-carboxylic acid tert-butyl ester are dissolved in 10 mL acetonitrile. 432 □L TMSCl and 565 mg potassium iodide are added. The reaction mixture is heated to reflux for 3 hours. After cooling to rt, 1 mL conc. HCl is added and the reaction mixture stirred for 1 hour. Then the mixture was concentrated in vacuo. Purification by HPLC and addition of 1 N aq. HCl before lyophilisation affords 53 mg (13%) 6-(4-hydroxy-3,5-dimethyl-phenyl)-4-[6-(4-methyl-piperazin-1-ylmethyl)-1H-indol-2-yl]-2H-pyridazin-3-one as its chloride salt.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 3 hours
  3. concentrationThen the mixture was concentrated in vacuo
  4. customPurification
  5. additionby HPLC and addition of 1 N aq. HCl before lyophilisation

Sources & evidence

ORD record
ord-2825d72b430646a7a4ef25137a60537c
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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