Sodium Hydroxide → 2-(3-Sulfamoyl-phenylamino)-5,6-dihydro-thieno[2,3-h] quinazoline-8-carboxylic acid tert-butyl ester

HRID 2063754Notes

Reaction equation

HRID 2063754 reaction equation
[C:1]([O:5][C:6]([C:8]1[S:12][C:11]2[CH2:13][CH2:14][C:15](=[CH:18]N(C)C)[C:16](=O)[C:10]=2[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH:23]([C:27]1[CH:28]=[C:29]([S:33]([NH2:36])(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1)[C:24]([NH2:26])=[NH:25].[OH-].[Na+]>C(O)(C)C.O>[C:1]([O:5][C:6]([C:8]1[S:12][C:11]2[CH2:13][CH2:14][C:15]3[CH:18]=[N:25][C:24]([NH:23][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([S:33](=[O:34])(=[O:35])[NH2:36])[CH:28]=4)=[N:26][C:16]=3[C:10]=2[CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 674064945-Dimethylaminomethylene-4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylic acid tert-butyl esterHCID 178479386HCID 178479386, compound

Product 1

HCID 592628022-(3-Sulfamoyl-phenylamino)-5,6-dihydro-thieno[2,3-h] quinazoline-8-carboxylic acid tert-butyl esterYield 53.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

5-Dimethylaminomethylene-4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylic acid tert-butyl ester (6.21 g, 20.20 mmol), 3-guanidinophenylsulphonamide hydrochloride (5.07 g, 20.20 mmol) and sodium hydroxide (0.81 g, 20.20 mmol) were suspended in isopropanol (250 mL) and stirred at reflux overnight. The reaction was allowed to cool to room temperature and diluted with water (˜200 mL). The resulting precipitate was isolated by filtration and the solid obtained was washed with water (1×100 mL), isopropanol (1×50 mL), diethyl ether (2×50 mL) and pentane (3×100 mL). Air drying gave an ochre powder (4.92 g, 53% yield). MS (ES+)459. δH (d6 DMSO) 1.5-1.6 (9H, s), 2.9-3.0 (2H, m), 3.1-3.2 (2H, m), 7.2-7.3 (2H, br s), 7.3-7.5 (2H, m), 7.7-7.8 (1H, m), 8.1 (1H, s), 8.4 (1H, s), 8.6 (1H, s), 9.9 (1H, s).

Workup

  1. temperatureat reflux overnight
  2. customThe resulting precipitate was isolated by filtration
  3. customthe solid obtained
  4. washwas washed with water (1×100 mL), isopropanol (1×50 mL), diethyl ether (2×50 mL) and pentane (3×100 mL)
  5. customAir drying

Sources & evidence

ORD record
ord-7cc4587798904bc299697b15a195f1c3
Source dataset
uspto-grants-2012_10
Patent number
US08288400B2

Reaction notes

Loading…