Ethanol → N-{2-[(2-Amino-3-benzyl-2,3-dihydro-1H-inden-5-yl)oxy]ethyl}-1-methyl-imidazole-4-sulfonamide hydrochloride
Reaction equation
[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][CH2:19][NH:20][S:21]([C:24]3[N:25]=[CH:26][N:27]([CH3:29])[CH:28]=3)(=[O:23])=[O:22])[CH:15]=2)[CH2:10][CH:9]1[NH:30]C(=O)OCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].C(O)C.[ClH:41].C(OCC)C>[Cl-].[Na+].O>[ClH:41].[NH2:30][CH:9]1[CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][CH2:19][NH:20][S:21]([C:24]3[N:25]=[CH:26][N:27]([CH3:29])[CH:28]=3)(=[O:23])=[O:22])[CH:15]=2)[CH2:10]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To ethyl 1-benzyl-6-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-2,3-dihydro-1H-inden-2-ylcarbamate (33 mg, 0.066 mmol; see example 195) was added 2N potassium hydroxide in ethanol (4 mL, 8.00 mmol) and stirred at 90° C. for 1 h. 50% brine was added and extracted twice with dichloromethane. The combined organic layers were washed with brine, dried, filtered and evaporated to obtain a clear oil m=27.3 mg. Added 2N hydrochloric acid/diethyl ether and stirred at room temperature for 2 h, filtered, washed with diethyl ether and dried to obtain the desired product as a white solid. m=8.6 mg (28%)
Workup
- extractionextracted twice with dichloromethane
- washThe combined organic layers were washed with brine
- customdried
- filtrationfiltered
- customevaporated
- customto obtain a clear oil m=27.3 mg
- stirringstirred at room temperature for 2 h
- filtrationfiltered
- washwashed with diethyl ether
- customdried
Sources & evidence
- ORD record
- ord-c5ded18b65204ca9b101bbed6c67fb91
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227930B2
Reaction notes
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