Sodium Hydroxide → HCID 11618895, compound
Reaction equation
C[O:2][C:3]([C:5]1[N:6]=[CH:7][N:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][C:19]=2[C:20]([F:23])([F:22])[F:21])[NH:16][C:15](=[O:24])[N:14]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[C:13]3=[O:30])[CH:9]=1)=[O:4].[OH-].[Na+]>CN(C)C=O>[CH3:29][S:26]([NH:25][N:14]1[C:13](=[O:30])[C:12]2[C:17](=[CH:18][C:19]([C:20]([F:21])([F:22])[F:23])=[C:10]([N:8]3[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[N:6]=[CH:7]3)[CH:11]=2)[NH:16][C:15]1=[O:24])(=[O:28])=[O:27]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 1-(3-methanesulfonylamino-2,4-dioxo-7-trifluoromethyl-1,2,3,4-tetrahydro-quinazolin-6-yl)-1H-imidazole-4-carboxylic acid methyl ester (150 mg, 0.335 mmol) in 10 ml dimethylformamide are added 1.7 ml of 1 M aqueous sodium hydroxide solution and stirred at room temperature for one hour and at 50° C. for two hours. After cooling to room temperature the solvent is evaporated in vacuo, the residue taken up in water, acidified with 5 ml of 1 M hydrochloric acid and extracted three times with 15 ml each of dichloromethane. The organic layer is dried over sodium sulfate, filtered and evaporated to give 126 mg (0.29 mmol, 87%) of amorphous 1-(3-methanesulfonylamino-2,4-dioxo-7-trifluoromethyl-1,2,3,4-tetrahydro-quinazolin-6-yl)-1H-imidazole-4-carboxylic acid, ES-MS: m/z 434 [M+H]+.
Workup
- temperatureAfter cooling to room temperature the solvent
- customis evaporated in vacuo
- extractionextracted three times with 15 ml each of dichloromethane
- dry with materialThe organic layer is dried over sodium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-3b3313673d114cc593e040601ea9378a
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299085B2
Reaction notes
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