HCID 10576377, compound → HCID 11798109, compound

HRID 1738496Notes

Reaction equation

HRID 1738496 reaction equation
[Br:1][C:2]1[C:3]([CH3:27])=[N:4][O:5][C:6]=1[NH:7][S:8]([C:11]1[CH:15]=[CH:14][S:13][C:12]=1[C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)=O)(=[O:10])=[O:9]>C1COCC1>[Br:1][C:2]1[C:3]([CH3:27])=[N:4][O:5][C:6]=1[NH:7][S:8]([C:11]1[CH:15]=[CH:14][S:13][C:12]=1[CH2:16][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)(=[O:10])=[O:9]

Participants

3

Reactant 1

HCID 10576377HCID 10576377, compound

Product 1

HCID 11798109HCID 11798109, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

BH3 -THF (15 ml, 1 M 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-92c327fe4bc648f7ae96036c5a982210
Source dataset
uspto-grants-1999_10
Patent number
US05962490

Reaction notes

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