Triethylamine → N-(5-(benzo[c][1,2,5]oxadiazol-5-yloxy)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

HRID 473091ノート

反応式

HRID 473091 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:17]=[CH:16][C:12]3=[N:13][O:14][N:15]=[C:11]3[CH:10]=2)O1.[OH:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[CH:25]([NH:29][S:30]([CH:33]([CH3:35])[CH3:34])(=[O:32])=[O:31])[CH2:24][CH2:23]2.C(N(CC)CC)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[N:13]1[O:14][N:15]=[C:11]2[CH:10]=[C:9]([O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[CH:25]([NH:29][S:30]([CH:33]([CH3:35])[CH3:34])(=[O:32])=[O:31])[CH2:24][CH2:23]4)[CH:17]=[CH:16][C:12]=12

参加物

6

反応物 3

HCID 8471TriethylamineHCID 467380042,1,3-Benzoxadiazole-5-boronic acid, pinacol esterHCID 70223457N-(5-hydroxy-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

生成物 1

HCID 70223362N-(5-(benzo[c][1,2,5]oxadiazol-5-yloxy)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]oxadiazole (0.313 mmol, 77 mg), N-(5-hydroxy-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide (0.157 mmol, 40 mg), copper (II)acetate (0.157 mmol, 28.5 mg), triethylamine (0.783 mmol, 0.110 mL, 79 mg) and 4A molecular sieves (100 mg) in DCM (1 mL) was stirred at room temperature for 60 h. The reaction mixture was filtered through dicalite and the pad washed with MeOH before the filtrate was concentrated to dryness. The residue was purified by prep HPLC to give a brown film (32. mg, 5.5%). MS (ESI): m/z [M+H]+ 374.0

後処理

  1. filtrationThe reaction mixture was filtered through dicalite
  2. washthe pad washed with MeOH before the filtrate
  3. concentrationwas concentrated to dryness
  4. customThe residue was purified by prep HPLC
  5. customto give a brown film (32. mg, 5.5%)

出典と根拠

ORDレコード
ord-88de6eda68fc4e83922d2c0746be78ac
出典データセット
uspto-grants-2014_01
特許番号
US08633237B2

反応ノート

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