(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → 3-(5-chloromethyl-[1,3,4]oxadiazol-2-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole
Reaction equation
[Cl:1][CH2:2][C:3]([NH:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[C:13]([O:18][CH3:19])[CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:10]=1)=O)=[O:4].[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>O1CCCC1>[Cl:1][CH2:2][C:3]1[O:4][C:7]([C:9]2[C:17]3[C:12](=[C:13]([O:18][CH3:19])[CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:10]=2)=[N:6][N:5]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid N′-(2-chloroacetyl)hydrazide (250 mg, 0.662 mmol) in tetrahydrofuran (3 ml) was added (methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt (315 mg, 1.32 mmol) and the resulting reaction mixture subjected to microwave irradiation at 150° C. for 15 minutes. The reaction mixture was quenched with methanol and the solvent evaporated. The resulting residue was purified by flash chromatography using 33-50% (v/v) ethyl acetate in heptane to give 3-(5-chloromethyl-[1,3,4]oxadiazol-2-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole (169 mg, 0.47 mmol) as a yellow solid. This reaction was repeated on a 0.53 mmol scale to afford the same intermediate (a total of 276 mg, 0.77 mmol).
Workup
- customthe resulting reaction mixture
- customirradiation at 150° C. for 15 minutes
- customThe reaction mixture was quenched with methanol
- customthe solvent evaporated
- customThe resulting residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-be1220f741bc400185263c1344fcd357
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700634B2
Reaction notes
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