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

HRID 473091노트

반응식

HRID 473091 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

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

후처리

  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%)

출처 및 근거

ORD 기록
ord-88de6eda68fc4e83922d2c0746be78ac
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633237B2

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