HCID 10131987, compound → HCID 22605936, compound

HRID 2307280Notes

Reaction equation

HRID 2307280 reaction equation
C([O:3][C:4](=O)[C:5]([NH:7][C:8]1[CH:13]=[C:12]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)[CH:11]=[C:10]([CH3:24])[N:9]=1)=[O:6])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][CH2:23][N:14]1[C:12]1[CH:11]=[C:10]([CH3:24])[N:9]=[C:8]([NH:7][C:5](=[O:6])[CH2:4][OH:3])[CH:13]=1

Participants

4

Reactant 2

HCID 10131987HCID 10131987, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22605936HCID 22605936, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[4-(3,4-dihydro-1H-isoquinolin-2-yl)-6-methyl-pyridin-2-yl]-oxalamic acid ethyl ester (example 33) (0.43 g, 1.3 mmol) in THF (20 ml) was cooled in an ice bath and lithium aluminum hydride (0.12 g, 3.2 mmol) was added in. The mixture was stirred at rt for 2 hr, quenched with saturated aqueous Seignette-salt solution and filtered. The organic phase was dried (Na2SO4) and concentrated. After chromatograpy (SiO2 with CH2Cl/CH3OH/NH4OH=200/10/1) the title compound was obtained as a colorless oil (0.18 g, 47%). Mp. 160-162° C. (AcOEt), MS: m/e=296(M−H−).

Workup

  1. customquenched with saturated aqueous Seignette-salt solution
  2. filtrationfiltered
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-73153206329e4e3daec73fa3ccacdbf2
Source dataset
uspto-grants-2004_12
Patent number
US06831087B2

Reaction notes

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