8-(3-Sulfamoyl-phenylamino)-thiazolo[4,5-h]quinazoline-2-carboxylic acid ethyl ester → 8-(3-Sulfamoyl-phenylamino)-thiazolo[4,5-h]quinazoline-2-carboxylic acid

HRID 908350Notes

Reaction equation

HRID 908350 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]2[C:17]3[N:16]=[C:15]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([S:25](=[O:28])(=[O:27])[NH2:26])[CH:20]=4)[N:14]=[CH:13][C:12]=3[CH:11]=[CH:10][C:9]=2[N:29]=1)=[O:5])C>CCO.[OH-].[Na+]>[S:25]([C:21]1[CH:20]=[C:19]([NH:18][C:15]2[N:14]=[CH:13][C:12]3[CH:11]=[CH:10][C:9]4[N:29]=[C:6]([C:4]([OH:5])=[O:3])[S:7][C:8]=4[C:17]=3[N:16]=2)[CH:24]=[CH:23][CH:22]=1)(=[O:28])(=[O:27])[NH2:26]

Participants

4

Reactant 1

HCID 592629448-(3-Sulfamoyl-phenylamino)-thiazolo[4,5-h]quinazoline-2-carboxylic acid ethyl ester

Product 1

HCID 114864308-(3-Sulfamoyl-phenylamino)-thiazolo[4,5-h]quinazoline-2-carboxylic acidYield 102.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

8-(3-Sulfamoyl-phenylamino)-thiazolo[4,5-h]quinazoline-2-carboxylic acid ethyl ester (494 mg, 1.15 mmol) was suspended in a mixture of EtOH (30 ml) and 1N sodium hydroxide (20 ml). The mixture was stirred at room temperature for 12 h. EtOH was removed in vacuo and the residual crude mixture was neutralised with 1N HCl (20 ml). The resulting solid was filtered and dried under vacuo to afford 0.473 g of a brownish solid. MS (ES+) 402, (ES−) 400. δH (d6 DMSO) 7.37 (2H, s), 7.50 (1H, d), 7.60 (1H, t), 8.06 (2H, s), 8.16 (1H, d), 8.62 (1H, s), 9.50 (1H, s), 10.52 (1H, s), 14.80 (1H, br s).

Workup

  1. customEtOH was removed in vacuo
  2. filtrationThe resulting solid was filtered
  3. customdried under vacuo

Sources & evidence

ORD record
ord-27eef778b7154e60b05396ec4e7719d1
Source dataset
uspto-grants-2011_09
Patent number
US08017619B2

Reaction notes

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