1,1'-Carbonyldiimidazole → 2-{2-[3-cyclohexyl-6-(1H-imidazol-1-ylcarbonyl)-1-methyl-1H-indol-2-yl]phenoxy}-N-methyl-N-(2-{2-[methyl(sulfamoyl)amino]ethoxy}ethyl)acetamide

HRID 1807636Notes

Reaction equation

HRID 1807636 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)(N1C=CN=C1)=[O:2].[CH:13]1([C:19]2[C:27]3[C:22](=[CH:23][C:24](C(O)=O)=[CH:25][CH:26]=3)[N:21]([CH3:31])[C:20]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[O:38][CH2:39][C:40]([N:42]([CH3:54])[CH2:43][CH2:44][O:45][CH2:46][CH2:47][N:48]([CH3:53])[S:49](=[O:52])(=[O:51])[NH2:50])=[O:41])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C(#N)C>[CH:13]1([C:19]2[C:27]3[C:22](=[CH:23][C:24]([C:1]([N:8]4[CH:12]=[CH:11][N:10]=[CH:9]4)=[O:2])=[CH:25][CH:26]=3)[N:21]([CH3:31])[C:20]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[O:38][CH2:39][C:40]([N:42]([CH3:54])[CH2:43][CH2:44][O:45][CH2:46][CH2:47][N:48]([CH3:53])[S:49](=[O:52])(=[O:51])[NH2:50])=[O:41])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 583178273-cyclohexyl-1-methyl-2-(2-{2-[methyl(2-{2-[methyl(sulfamoyl)amino]ethoxy}ethyl)amino]-2-oxoethoxy}phenyl)-1H-indole-6-carboxylic acid

Product 1

HCID 583178162-{2-[3-cyclohexyl-6-(1H-imidazol-1-ylcarbonyl)-1-methyl-1H-indol-2-yl]phenoxy}-N-methyl-N-(2-{2-[methyl(sulfamoyl)amino]ethoxy}ethyl)acetamideYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Carbonyldiimidazole (405 mg, 2.50 mmol) was added to a stirred solution of intermediate 8 (300 mg, 0.50 mmol) in dry acetonitrile (CH3CN) (25 mL). The reaction mixture was stirred at room temperature for 1 h, upon which complete conversion was observed. The resulting solution was evaporated and the residue was purified by silica flash chromatography (gradient AcOEt/CH3CN 1:0 to 0:1) to yield 315 mg (97%) of 2-{2-[3-cyclohexyl-6-(1H-imidazol-1-ylcarbonyl)-1-methyl-1H-indol-2-yl]phenoxy}-N-methyl-N-(2-{2-[methyl(sulfamoyl)amino]ethoxy}ethyl)acetamide 9 as a white powder: m/z=651 (M+H)+.

Workup

  1. customThe resulting solution was evaporated
  2. customthe residue was purified by silica flash chromatography (gradient AcOEt/CH3CN 1:0 to 0:1)

Sources & evidence

ORD record
ord-08c42520982b4cba8969f4f8d4ca66a4
Source dataset
uspto-grants-2013_01
Patent number
US08357687B2

Reaction notes

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