Methanol → HCID 44465021, compound

HRID 1850823Notes

Reaction equation

HRID 1850823 reaction equation
[Cl:1][C:2]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][N:16]=[C:17]2[C:20]2([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[CH2:23][CH2:22][CH2:21]2)=[CH:12][CH:11]=1)=[O:5].[BH4-].[Na+].CO>O>[Cl:1][C:2]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][NH:16][CH:17]2[C:20]2([C:24]3[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=3)[CH2:23][CH2:22][CH2:21]2)=[CH:12][CH:11]=1)=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 66868904HCID 66868904, compound

Product 1

HCID 44465021HCID 44465021, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2,4-dichloro-N-(2-{1-[1-(4-chloro-phenyl)-cyclobutyl]-3,4-dihydro-isoquinolin-7-yloxy}-ethyl)-benzamide (80.0 mg, 0.15 mmol) and sodium borohydride (12.0 mg, 0.32 mmol) were dissolved in H2O (10 ml) and MeOH (0.5 ml) and stirred for 14 h at RT. Water was added and the mixture was extracted with ethyl acetate. The organic layers were washed with water and saturated NaCl solution, dried with MgSO4, and the solvent was removed. The residue was transferred into the hydrochloride salt using HCl dissolved in isopropanole (6 molar solution). Crystallization gave 2,4-Dichloro-N-(2-{1-[1-(4-chloro-phenyl)-cyclobutyl]-1,2,3,4-tetrahydro-isoquinolin-7-yloxy}-ethyl)-benzamide (60.0 mg, 0.11 mmol, 70%) as white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layers were washed with water and saturated NaCl solution
  3. dry with materialdried with MgSO4
  4. customthe solvent was removed
  5. dissolutiondissolved in isopropanole (6 molar solution)
  6. customCrystallization

Sources & evidence

ORD record
ord-da04681f1f014150ad2f94f2ca28f4c0
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

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