Acetone → HCID 9909759, compound

HRID 1635992Notes

Reaction equation

HRID 1635992 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH2:18][C:19]3=[O:24])=[CH:12][CH:13]=1)=[O:6].[BH4-].[Na+].CC(C)=O>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH2:18][CH:19]3[OH:24])=[CH:12][CH:13]=1)=[O:6]

Participants

6

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydride2×HCID 9909644HCID 9909644, compound

Product 1

HCID 9909759HCID 9909759, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

After 413 mg of 3,4-dichloro-N1-{6-[(1-oxo-2,3-dihydro-1H-inden-4-yl)oxy]-3-pyridinyl}benzamide was dissolved in a mixed solvent of 4 ml of tetrahydrofuran and 1 ml of water, 23 mg of sodium tetrahydroborate was added and the mixture was stirred at room temperature. After 4 hours, acetone was added to the reaction solution to decompose excess sodium tetrahydroborate. Then, water was added and the solution was extracted with ethyl acetate. The organic (ethyl acetate) layer was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. To the resulting oily substance, diethyl ether was added and the deposited crystal was isolated by filtration to obtain 289 mg of the titled compound.

Workup

  1. additionwas added
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic (ethyl acetate) layer was washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the resulting oily substance, diethyl ether was added
  7. customthe deposited crystal was isolated by filtration

Sources & evidence

ORD record
ord-2f980059d5374ee799518389d2f29c43
Source dataset
uspto-grants-2003_01
Patent number
US06511995B1

Reaction notes

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