Bumetanide → HCID 16657240, compound

HRID 1676908Notes

Reaction equation

HRID 1676908 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[C:8]([C:23]([OH:25])=[O:24])[CH:9]=[C:10]([S:19]([NH2:22])(=[O:21])=[O:20])[C:11]=1[O:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1.[CH2:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C>CN(C)C=O.ClCCl>[NH2:22][S:19]([C:10]1[CH:9]=[C:8]([CH:7]=[C:6]([NH:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:11]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])(=[O:21])=[O:20]

Participants

6

Reactant 3

HCID 2471BumetanideHCID 7503Benzyl ChlorideHCID 8471Triethylamine

Product 1

HCID 16657240HCID 16657240, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Bumetanide (1.15 g, 3.15 mmol) was dissolved in dimethylformamide (DMF, 10 mL) and benzyl chloride (400 uL, 2.8 mmol) was added followed by triethylamine (480 uL). The reaction was heated to 80° C. for 12 hours, at which time TLC and LC/MS indicated the reaction was complete. The reaction was cooled to room temperature, brought up in dichloromethane and washed with water, saturated ammonium chloride and concentrated to a thick slurry. To the slurry was added water (25 mL). The resultant solids were filtered and dried in a vacuum oven at 50° C. for 12 hours to yield 1.0 g (80%) of benzyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with water, saturated ammonium chloride
  3. concentrationconcentrated to a thick slurry
  4. additionTo the slurry was added water (25 mL)
  5. filtrationThe resultant solids were filtered
  6. customdried in a vacuum oven at 50° C. for 12 hours

Sources & evidence

ORD record
ord-03845db6a44a456aae362aaa48041410
Source dataset
uspto-grants-2011_08
Patent number
US08008283B2

Reaction notes

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