Lithium Hydroxide → HCID 18393035, compound

HRID 1739420Notes

Reaction equation

HRID 1739420 reaction equation
C([O:4][CH2:5][C@@H:6]1[CH2:15][C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([O:16][CH3:17])[CH:13]=2)[C:8]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([N:26]3[N:35]=[C:34]([C:36]4[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=4)[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:27]3=[O:42])[CH:21]=2)=[N:7]1)(=O)C.[OH-].[Li+]>CO.O1CCCC1>[OH:4][CH2:5][C@@H:6]1[CH2:15][C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([O:16][CH3:17])[CH:13]=2)[C:8]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([N:26]3[N:35]=[C:34]([C:36]4[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=4)[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:27]3=[O:42])[CH:21]=2)=[N:7]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 18393037HCID 18393037, compound

Product 1

HCID 18393035HCID 18393035, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(3S)-4-(3-Acetoxymethyl-3,4-dihydro-6,7-dimethoxyisoquinolin-1-yl)-2-[4-(3-pyridyl)phthalazin-1(2H)-on-2-yl]pyridine (400 mg) is suspended in a mixture of methanol (20 ml) and tetrahydrofuran (10 ml), and thereto is added dropwise a 1 M aqueous lithium hydroxide solution (1.43 ml) under ice-cooling. The mixture is stirred for 15 minutes under ice-cooling, and the mixture is reacted at room temperature for three hours. The reaction mixture is concentrated, and the water is added to the residue. The mixture is extracted with methylene chloride, and the extract is washed, dried and concentrated. The reside is purified by silica gel column chromatography (solvent; chloroform:methanol=10:1) to give (3S)-4-(3,4-dihydro-3-hydroxymethyl-6,7-dimethoxyisoquinolin-1-yl)-2-[4-(3-pyridyl)phthalazin-1(2H)-on-2-yl]pyridine (230 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customthe mixture is reacted at room temperature for three hours
  4. concentrationThe reaction mixture is concentrated
  5. additionthe water is added to the residue
  6. extractionThe mixture is extracted with methylene chloride
  7. washthe extract is washed
  8. customdried
  9. concentrationconcentrated
  10. customThe reside is purified by silica gel column chromatography (solvent; chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-dafe51dbaae74e1d8be3e5d0c354caff
Source dataset
uspto-grants-1999_10
Patent number
US05965730

Reaction notes

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