Sodium cyanoborohydride → HCID 21963709, compound

HRID 2212203Notes

Reaction equation

HRID 2212203 reaction equation
I.[Cl:2][C:3]1[C:4]2[C:5]3[C:6](=[C:20]([CH3:23])[O:21][N:22]=3)[C:7](=[O:19])[N:8]([CH:13]3[CH2:18][CH2:17][CH2:16]N[CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1.[C:24]([BH3-])#[N:25].[Na+]>CO>[Cl:2][C:3]1[C:4]2[C:5]3[C:6](=[C:20]([CH3:23])[O:21][N:22]=3)[C:7](=[O:19])[N:8]([CH:13]3[CH2:18][CH2:17][CH2:16][N:25]([CH2:24][CH2:6][CH2:5][C:4]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:3]=4)[CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 219637129-Chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

Product 1

HCID 21963709HCID 21963709, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 9-chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide (50 mg, 0.11 mmol) in methanol (3 mL) add approximately 100 mg of finely ground 3 Å sieves and stir the mixture for 30 minutes at room temperature. To the suspension add sodium cyanoborohydride (21 mg, 0.34 mmol) and stir the mixture at room temperature under nitrogen overnight. Concentrate the solution and dissolve in 20% isopropanol/chloroform, wash with saturated aqueous sodium bicarbonate solution, brine, dry over magnesium sulfate and concentrate. Purify by flash chromatography on silica gel (eluting with 0–1% methanol/chloroform) to give 23.9 mg of the title compound as a yellow foam, 49% yield. 1H NMR: consistent with structure. MS (ion spray) 436 (M+).

Workup

  1. additionadd approximately 100 mg of finely ground 3 Å sieves
  2. stirringstir the mixture at room temperature under nitrogen overnight
  3. concentrationConcentrate the solution
  4. dissolutiondissolve in 20% isopropanol/chloroform
  5. washwash with saturated aqueous sodium bicarbonate solution, brine
  6. dry with materialdry over magnesium sulfate
  7. concentrationconcentrate
  8. customPurify by flash chromatography on silica gel (eluting with 0–1% methanol/chloroform)

Sources & evidence

ORD record
ord-d0ea1f22881a4cec857a3f5524f2f641
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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