2-Pyridin-2-yl-3-quinolin-4-yl-pyrazolo[5,1-c]morpholin-4-one → 2-(2-Hydroxyethyl)-3-hydroxymethyl-5-pyridin-2-yl-4-quinolin-4-yl-pyrazole

HRID 8239

Reaction equation

HRID 8239 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:16]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)=[C:10]2[C:11](=[O:15])[O:12][CH2:13][CH2:14][N:9]2[N:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[OH:12][CH2:13][CH2:14][N:9]1[C:10]([CH2:11][OH:15])=[C:16]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:8]1

Participants

4

Reactant 2

HCID 99241292-Pyridin-2-yl-3-quinolin-4-yl-pyrazolo[5,1-c]morpholin-4-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 219926122-(2-Hydroxyethyl)-3-hydroxymethyl-5-pyridin-2-yl-4-quinolin-4-yl-pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-pyridin-2-yl-3-quinolin-4-yl-pyrazolo[5,1-c]morpholin-4-one (0.50 g, 1.46 mmol) in tetrahydrofuran (20 mL) is added LiAlH4 (0.50 g, 13.1 mmol) at room temperature. The mixture is stirred for 2 h quenched with 1 N sodium hydroxide solution, and partitioned between dichloromethane and water. The organic portion is dried (sodium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (10% methanol/dichloromethane) to yield the title compound, 0.35 g (70%), as an off-white solid.

Workup

  1. customquenched with 1 N sodium hydroxide solution
  2. custompartitioned between dichloromethane and water
  3. dry with materialThe organic portion is dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on SiO2 (10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-53a452ae6cce4174b0f114354aea1e18
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

Loading…