HCID 10159927, compound → HCID 10151029, compound

HRID 1295587Notes

Reaction equation

HRID 1295587 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][C:28](=O)[NH:27][C:26]=4[CH:32]=3)[CH2:17][CH2:16]2)[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][N:18]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][NH:27][C:26]=4[CH:32]=3)[CH2:19][CH2:20]2)[N:3]=1

Participants

4

Reactant 2

HCID 10159927HCID 10159927, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 10151029HCID 10151029, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6-(4-(2-(2-Methylquinolin-5-yloxy)ethyl)piperazin-1-ylmethyl)-4H-benzo[1,4]oxazin-3-one (0.139 g, 0.32 mmol) was dissolved in dry tetrahydrofuran (10 mL) under argon and treated with a solution of lithium aluminium hydride in tetrahydrofuran (1 M, 0.32 mL, 0.32 mmol) and the reaction stirred at ambient temperature. More lithium aluminium hydride solution (1 M in tetrahydrofuran, 0.32 mL, 0.32 mmol) was added after 18 h and the mixture stirred for 1 h before being quenched with 10% potassium sodium tartrate aq. and extracted with ethyl acetate. The combine organic extracts were washed with water, saturated brine, dried (MgSO4) and evaporated to dryness under reduced pressure. Chromatography on SiO2, eluting with a gradient of 10% 0.880 ammonia/methanol in dichloromethane, gave the title compound (0.073 g, 54%) as a yellow foam.

Workup

  1. stirringthe mixture stirred for 1 h
  2. custombefore being quenched with 10% potassium sodium tartrate aq.
  3. extractionextracted with ethyl acetate
  4. washThe combine organic extracts were washed with water, saturated brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness under reduced pressure
  7. washChromatography on SiO2, eluting with a gradient of 10% 0.880 ammonia/methanol in dichloromethane

Sources & evidence

ORD record
ord-1743eb91f1cf40ffa5dce4d198797ae0
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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