Tetrahydrofuran → HCID 57049731, compound

HRID 2270681Notes

Reaction equation

HRID 2270681 reaction equation
B.[CH2:2]1[CH2:6][O:5][CH2:4][CH2:3]1.[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]C1C=CC=C(OC)C=1)=O)(=[O:16])=[O:15].[CH2:34]1[CH2:38]OC[CH2:35]1>>[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[CH:22]([C:34]1[CH:38]=[CH:3][CH:2]=[C:6]([O:5][CH3:4])[CH:35]=1)[NH2:24])(=[O:15])=[O:16]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2723981Borane;tetrahydrofuranHCID 10576377HCID 10576377, compound

Product 1

HCID 57049731HCID 57049731, compoundYield 12%

Procedure

BH3THF (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-7ffd206cb9844352a1686d27a66b409e
Source dataset
uspto-grants-2001_12
Patent number
US06331637B1

Reaction notes

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