Benzyl Alcohol → HCID 178475034, compound

HRID 1913117Notes

Reaction equation

HRID 1913117 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C@H:13]3[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:22])[CH3:21])[CH2:15][CH2:14]3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH2:23]([OH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[H-].[Na+]>CC(N(C)C)=O>[CH2:23]([O:30][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C@H:13]3[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:22])[CH3:21])[CH2:15][CH2:14]3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 178475032HCID 178475032, compound

Product 1

HCID 178475034HCID 178475034, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

975 mg (3.06 mmol) of N-[4-(1-chloro-isoquinolin-6-yloxy)-cyclohexyl]-acetamide (18) were dissolved in 20 ml of dimethyl acetamide and 992 mg (9.17 mmol) of benzyl alcohol were added. After addition of 367 mg (9.17 mmol) of sodium hydride (60%), the reaction mixture was stirred for 3 h at room temperature and for 1 h at 80° C. Then, the solvent was removed in vacuo, the residue was dissolved in dichloromethane and washed three times with water. The organic layer was dried with magnesium sulfate and evaporated. Final purification by preparative HPLC yielded 680 mg of the title compound. Rt=1.75 min (Method B). Detected mass: 391.2 (M+H+).

Workup

  1. customThen, the solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed three times with water
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. customevaporated
  6. customFinal purification by preparative HPLC

Sources & evidence

ORD record
ord-863001d13d1f40ce8fa1dc1032ea32d5
Source dataset
uspto-grants-2013_12
Patent number
US08609691B2

Reaction notes

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