Carbon Dioxide → HCID 86612058, compound

HRID 2234122Notes

Reaction equation

HRID 2234122 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=O)[CH:15]=2)[CH:10]=[C:9]1[C:19]1[CH:24]=[C:23]([Cl:25])[N:22]=[N:21][C:20]=1[O:26][CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+].C(=O)=O>ClCCl.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][N:32]3[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]3)[CH:15]=2)[CH:10]=[C:9]1[C:19]1[CH:24]=[C:23]([Cl:25])[N:22]=[N:21][C:20]=1[O:26][CH3:27])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86612057HCID 86612057, compound

Product 1

HCID 86612058HCID 86612058, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

2.68 g 2-(6-Chloro-3-methoxy-pyridazin-4-yl)-6-formyl-indole-1-carboxylic acid tert-butyl ester is dissolved in 300 mL dichloromethane. 4.73 mL N-methylpiperazine and then 30 mL acetic acid are added. 4.40 g sodium triacetoxyborohydride is added in several portions over 3 hours. Sat. aq. NaHCO3-solution is added and the reaction mixture is stirred until the CO2-evolution stopped. The reaction mixture is diluted with dichloromethane, the aq. phase washed with dichloromethane, the combined org. phases dried (MgSO4) and concentrated in vacuo. HPLC purification affords 2.019 g (50%) 2-(6-chloro-3-methoxy-pyridazin-4-yl)-6-(4-methyl-piperazin-1-ylmethyl)-indole-1-carboxylic acid tert-butyl ester as its trifluoro-acetate salt.

Workup

  1. washthe aq. phase washed with dichloromethane
  2. dry with materialphases dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customHPLC purification

Sources & evidence

ORD record
ord-14d1cb07920548188af29beb0d97725e
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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