Sodium Bicarbonate → HCID 178437135, compound

HRID 1373069Notes

Reaction equation

HRID 1373069 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([CH:13]=[CH2:14])=[CH:5][N:6]=[C:7]2[Cl:12].[CH2:15]([N:22]([CH:30]1[CH2:35][CH2:34][C:33](=O)[CH2:32][CH2:31]1)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[BH4-].[Na+].C(=O)([O-])O.[Na+]>ClCCl.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C(OCC)(=O)C.CO>[CH2:15]([N:22]([C@H:30]1[CH2:31][CH2:32][C@H:33]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[C:4]([CH:13]=[CH2:14])=[CH:5][N:6]=[C:7]3[Cl:12])[CH2:34][CH2:35]1)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

9

Reactant 4

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 15342642HCID 15342642, compoundHCID 23112159HCID 23112159, compound

Product 1

HCID 178437135HCID 178437135, compoundYield 61.7%

Reagents, catalysts & solvents 4

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-amino-1-chloro-4-vinylisoquinoline (0.6 g) and Intermediate 9 (1.8 g) in dichloromethane (13 ml) was added with titanium tetraisopropoxide (1.7 ml) at room temperature, and stirred at room temperature for 22 hours. The reaction mixture was added with methanol (13 ml), and sodium borohydride (444 mg), and stirred at room temperature for two hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate (60 ml), and ethyl acetate (60 ml), and the precipitates were removed by filtration. Then, the organic layer was separated, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:acetone=5:4) to obtain the title compound (890 mg).

Workup

  1. stirringstirred at room temperature for two hours
  2. customthe precipitates were removed by filtration
  3. customThen, the organic layer was separated
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:acetone=5:4)

Sources & evidence

ORD record
ord-af34460b651c41f7b1b84eb284116ad9
Source dataset
uspto-grants-2007_01
Patent number
US07160894B2

Reaction notes

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