Isopropanol → HCID 86685972, compound

HRID 2277678Notes

Reaction equation

HRID 2277678 reaction equation
[CH3:1][CH:2]([OH:4])[CH3:3].[H-].[Na+].[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([C:19]1[CH:20]=[N:21][CH:22]=[C:23]([CH2:25]Cl)[CH:24]=1)[CH2:12][CH2:11]2>CN(C=O)C>[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([C:19]1[CH:20]=[N:21][CH:22]=[C:23]([CH2:25][O:4][CH:2]([CH3:3])[CH3:1])[CH:24]=1)[CH2:12][CH2:11]2

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 86685969HCID 86685969, compound

Product 1

HCID 86685972HCID 86685972, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To solution of propan-2-ol (3.6 mg, 0.06 mmol) in dry DMF (1 mL) was added NaH (1.5 mg, 0.06 mmol) at 0° C. The reaction mixture was stirred at room temperature for 5 min before 6-chloro-2-(5-chloromethyl-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-one (15 mg, 0.05 mmol, example 140 [A]) was added. The resulting reaction mixture was then stirred at room temperature for 1 hour before it was poured into ice-water and extracted with EtOAc (2×5 mL). The organic layer was dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was then purified by prep-HPLC to give title compound (8 mg, 48%) as a white solid. MS: 331.1 (M+H+).

Workup

  1. additionwas added
  2. customThe resulting reaction mixture
  3. extractionextracted with EtOAc (2×5 mL)
  4. customThe organic layer was dried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo
  7. customto give a crude product which
  8. customwas then purified by prep-HPLC

Sources & evidence

ORD record
ord-30f12ebb19ac44c2aedaddefc9a9df77
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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