Sodium triacetoxyborohydride → HCID 66703871, compound

HRID 426008Notes

Reaction equation

HRID 426008 reaction equation
Cl.[Cl:2][C:3]1[CH:23]=[CH:22][C:6]([C:7]([NH:9][C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][C:16](=[O:21])[N:17]3[CH3:20])=[CH:12][CH:11]=2)=[O:8])=[C:5]([NH:24][CH2:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][NH:27]2)[CH:4]=1.[C:32](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.CO.C=O>[ClH:2].[Cl:2][C:3]1[CH:23]=[CH:22][C:6]([C:7]([NH:9][C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][C:16](=[O:21])[N:17]3[CH3:20])=[CH:12][CH:11]=2)=[O:8])=[C:5]([NH:24][CH2:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][N:27]2[CH3:32])[CH:4]=1

Participants

6

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 66703606HCID 66703606, compound

Product 1

HCID 66703871HCID 66703871, compoundYield 87.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 712FormaldehydeSolventHCID 887MethanolSolvent

Procedure

4-Chloro-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-2-[(piperidin-2-ylmethyl)amino]benzamide hydrochloride (100 mg) was dissolved in a mixed solution of acetic acid (3 mL) and methanol (2 mL), and 1 ml of formaldehyde aqueous solution (36%) was added thereto. Sodium triacetoxyborohydride (252 mg) was added to this solution at 0° C., followed by stirring at room temperature for 30 minutes. After concentration under a reduced pressure, this was made basic by adding a saturated sodium bicarbonate aqueous solution, followed by extraction with chloroform. After drying the organic layer with magnesium sulfate, the solvent was evaporated under a reduced pressure. By purifying the residue by silica gel column chromatography (chloroform:methanol, 10:1) and treating the resulting free base with 4 M hydrogen chloride/ethyl acetate solution, 4-chloro-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-2-{[(1-methylpiperidin-2-yl)methyl]amino}benzamide hydrochloride (45 mg) was obtained as a solid.

Workup

  1. additionwas added
  2. concentrationAfter concentration under a reduced pressure
  3. additionby adding a saturated sodium bicarbonate aqueous solution
  4. extractionfollowed by extraction with chloroform
  5. dry with materialAfter drying the organic layer with magnesium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customBy purifying the residue by silica gel column chromatography (chloroform:methanol, 10:1)
  8. additiontreating the resulting free base with 4 M hydrogen chloride/ethyl acetate solution

Sources & evidence

ORD record
ord-3b689c93509d4649a872af0b9c8944c8
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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