3-Amino-5-methylisoxazole → HCID 57486825, compound

HRID 1911758Notes

Reaction equation

HRID 1911758 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([NH2:7])[CH:3]=1.[CH:8]1([CH2:12][N:13]([CH2:26][CH3:27])[C:14]2[C:23]([CH:24]=O)=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:11][CH2:10][CH2:9]1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH:8]1([CH2:12][N:13]([CH2:26][CH3:27])[C:14]2[C:23]([CH2:24][NH:7][C:4]3[CH:3]=[C:2]([CH3:1])[O:6][N:5]=3)=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 661723-Amino-5-methylisoxazoleHCID 5003444Sodium cyanoborohydrideHCID 574444442-[(Cyclobutylmethyl)(ethyl)amino]quinoline-3-carbaldehyde

Product 1

HCID 57486825HCID 57486825, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

5-Methyl-isoxazol-3-ylamine (0.098 g, 1 mmol) was added to a solution of 2-(cyclobutylmethyl-ethyl-amino)-quinoline-3-carbaldehyde (0.268 g, 1 mmol) in anhydrous methanol (5 mL) and acetic acid (0.15 mL) under nitrogen. After being stirred for 15 minutes at ambient temperature, sodium cyanoborohydride (0.19 g, 3 mmol) was added slowly, and the reaction mixture was stirred overnight. Afterwards, the solvent was evaporated in vacuo, and water (30 mL) and ethyl acetate (30 mL) were added to the residue. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with 1-5% methanol in dichloromethane, to afford the title compound (0.150 g, yield: 43%).

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customAfterwards, the solvent was evaporated in vacuo, and water (30 mL) and ethyl acetate (30 mL)
  3. additionwere added to the residue
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel
  10. washeluting with 1-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-0386ca1f13a74f3eb11394d6fa838af8
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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