Borane;tetrahydrofuran → HCID 11798109, compound

HRID 234408Notes

Reaction equation

HRID 234408 reaction equation
B.C1COCC1.[Br:7][C:8]1[C:9]([CH3:33])=[N:10][O:11][C:12]=1[NH:13][S:14]([C:17]1[CH:21]=[CH:20][S:19][C:18]=1[C:22]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=1)=O)(=[O:16])=[O:15]>C1COCC1>[Br:7][C:8]1[C:9]([CH3:33])=[N:10][O:11][C:12]=1[NH:13][S:14]([C:17]1[CH:21]=[CH:20][S:19][C:18]=1[CH2:22][NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 10576377HCID 10576377, compound

Product 1

HCID 11798109HCID 11798109, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BH3.THF (15 ml, 1M in THF) was added to a solution of N-(4-bromo-3-methyl-5-isoxazolyl)-2-[N-(3-methoxyphenyl)aminocarbonyl]thiophene-3-sulfonamide (Example 22) (1.0 g, 2.12 mmol) in dry THF (15 ml). The mixture was refluxed for 8 hours and cooled. THF was evaporated on a rotavap and MeOH was added to the residue. The resulting solution was concentrated. The final residue was purified by HPLC to give N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(3-methoxyphenyl)aminomethyl]thiophene-3-sulfonamide (113 mg., 12% yield) as a grey powder, m.p. 70°-73° C.

Workup

  1. temperatureThe mixture was refluxed for 8 hours
  2. temperaturecooled
  3. customTHF was evaporated on a rotavap
  4. additionMeOH was added to the residue
  5. concentrationThe resulting solution was concentrated
  6. customThe final residue was purified by HPLC

Sources & evidence

ORD record
ord-ba08ee7663c2493bbdbfe31391068032
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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