Hydrochloric Acid → HCID 57551752, compound

HRID 907266

Reaction equation

HRID 907266 reaction equation
[CH:1]1([NH:4][C:5](=[O:24])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[NH:18][CH:17]=[CH:16]4)[CH:7]=2)[CH2:3][CH2:2]1.[H-].[Na+].C([O:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37]Cl)=[CH:33][CH:32]=1)(=O)C.[OH-].[Na+].Cl>CN(C=O)C>[CH:1]1([NH:4][C:5](=[O:24])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:37][C:34]3[CH:35]=[CH:36][C:31]([OH:30])=[CH:32][CH:33]=3)[CH:17]=[CH:16]4)[CH:7]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24758Sodium hydride2×HCID 1483124-(Chloromethyl)phenyl acetateHCID 25020457N-Cyclopropyl-4-methyl-3-(1-oxo-1,2-dihydro-isoquinolin-6-yl)-benzamide

Product 1

HCID 57551752HCID 57551752, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of Example 11 (460 mg) in DMF (10 mL) was added 60% sodium hydride (38 mg) and the reaction stirred at room temperature for 30 minutes before the addition of 4-(chloromethyl)phenyl acetate (280 mg). The reaction mixture was then stirred at room temperature for 17 hrs. Additional 60% sodium hydride (38 mg) was added and the reaction was stirred for a further 2 hours. NaOH (5N, 2 mL) was added and the reaction was stirred at room temperature for 90 minutes. The reaction mixture was acidified with HCl (2N) and extracted into ethyl acetate. The organics were washed with water and brine, dried over magnesium sulphate and evaporated to yield the sub-titled compound (500 mg).

Workup

  1. stirringthe reaction was stirred for a further 2 hours
  2. stirringthe reaction was stirred at room temperature for 90 minutes
  3. extractionextracted into ethyl acetate
  4. washThe organics were washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-ab50e612b55a46608ff4714e6bba7b26
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Linked notes

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