1,3-Benzodioxole-5-carboxylic acid → HCID 10839533, compound

HRID 1166924Notes

Reaction equation

HRID 1166924 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([OH:24])(=O)[C:14]1[CH:22]=[CH:21][C:20]2[O:19][CH2:18][O:17][C:16]=2[CH:15]=1.[Br:25][C:26]1[C:27]([CH3:43])=[N:28][O:29][C:30]=1[NH:31][S:32]([C:35]1[CH:39]=[CH:38][S:37][C:36]=1[C:40]([NH2:42])=[O:41])(=[O:34])=[O:33].[H-].[Na+]>C1COCC1.O>[Br:25][C:26]1[C:27]([CH3:43])=[N:28][O:29][C:30]=1[NH:31][S:32]([C:35]1[CH:39]=[CH:38][S:37][C:36]=1[C:40]([NH:42][C:13](=[O:24])[C:14]1[CH:22]=[CH:21][C:20]2[O:19][CH2:18][O:17][C:16]=2[CH:15]=1)=[O:41])(=[O:34])=[O:33]

Participants

7

Reactant 4

HCID 71961,3-Benzodioxole-5-carboxylic acidHCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 10546830HCID 10546830, compound

Product 1

HCID 10839533HCID 10839533, compoundYield 3.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Carbonyldiimidazole (213 mg. 1.31 mmol) was added to a solution of piperonylic acid (181.5 mg., 1.09 mmol) in dry THF (10 ml). The resulting mixture was stirred for 15 minutes. N-(4-bromo-3-methyl-5-isoxazolyl)-2-aminocarbonylthiophene-3-sulfonamide (Example 89) (400 mg, 1.09 mmol) and NaH (175 mg, 60% in mineral oil, 4.37 mmol) were added sequentially. The mixture was stirred at room temperature for 8 hours. Water was added to destroy the excess NaH. The solvent was then evaporated and the residue was partitioned between 1N HCl and EtOAc. The organic layer was dried (MgSO4), the solid filtered and the filtrate concentrated. The residue was recrystallized from EtOAc to give N-(4-bromo-3-methyl-5-isoxazolyl)-2-{[(3,4-methylenedioxy)benzoyl]aminocarbonyl}thiophene-3-sulfonamide (20 mg, 3.6% yield) as a yellowish powder (m.p. 90-93° C.).

Workup

  1. stirringThe mixture was stirred at room temperature for 8 hours
  2. customto destroy the excess NaH
  3. customThe solvent was then evaporated
  4. customthe residue was partitioned between 1N HCl and EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationthe solid filtered
  7. concentrationthe filtrate concentrated
  8. customThe residue was recrystallized from EtOAc

Sources & evidence

ORD record
ord-d6bcad9f47bf40c58e195cd1f7f0b008
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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