Sulfuric Acid → HCID 17902007, compound

HRID 1934719Notes

Reaction equation

HRID 1934719 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:8]=1[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([Cl:21])[CH:14]=1)=[O:10].[C:27]1(=O)[CH2:31][CH2:30][CH2:29][CH2:28]1.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.O>[ClH:21].[Br:26][C:23]1[CH:24]=[CH:25][C:7]([NH:6][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:8]([CH:22]=1)[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([Cl:21])[CH:14]=1)=[O:10]

Participants

8

Reactant 5

HCID 1118Sulfuric Acid2×HCID 8452Cyclopentanone2×HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride2×HCID 22467517HCID 22467517, compound

Product 1

HCID 17902007HCID 17902007, compoundYield 155.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 97% sulfuric acid (79 mg) in tetrahydrofuran (0.5 mL) was added to a mixture of 2-amino-5-bromo-N-(3-chloro-4-methoxybenzyl)benzamide (199 mg), cyclopentanone (68 mg) and sodium borohydride (31 mg) in tetrahydrofuran (3 mL). The mixture was stirred for an hour at ambient temperature. Then cyclopentanone (68 mg), sodium borohydride (31 mg) and a solution of 97% sulfuric acid (80 mg) in tetrahydrofuran (0.5 mL) were added to the reaction mixture. After stirring for additional 2 hours at ambient temperature, the reaction mixture was diluted with water. The resultant was made alkaline with an aqueous saturated sodium bicarbonate solution and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by a preparative silica gel thin layer chromatography developed by 25% ethyl acetate in hexane. The obtained substance was dissolved in diethyl ether, and 4 N-hydrogen chloride solution in ethyl acetate (0.3 mL) was added thereto. The mixture was concentrated in vacuo and the residue was triturated with diethyl ether to give 5-bromo-N-(3-chloro-4-methoxybenzyl)-2-(cycloperitylamino)benzamide hydrochloride (198 mg) as white powders.

Workup

  1. stirringAfter stirring for additional 2 hours at ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a preparative silica gel thin layer chromatography
  7. dissolutionThe obtained substance was dissolved in diethyl ether
  8. addition4 N-hydrogen chloride solution in ethyl acetate (0.3 mL) was added
  9. concentrationThe mixture was concentrated in vacuo
  10. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-c2a2569fbc6c43eda21b0d2f339224fb
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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