Dimethylformamide → 2-Methoxy-6-(6-methoxy-4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)benzofuran-2-yl)imidazo[2,1-b][1,3,4]thiadiazole

HRID 625113

反応式

HRID 625113 の反応式
[CH3:1][O:2][C:3]1[S:7][C:6]2=[N:8][C:9]([C:11]3[O:12][C:13]4[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH2:23][C:24]#[CH:25])[C:14]=4[CH:15]=3)=[CH:10][N:5]2[N:4]=1.[N:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[N+:27]=[N-:28].CN(C=O)C.O[C@H]([C@@H]1C([O-])=C(O)C(=O)O1)CO.[Na+]>ClCCl.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][O:2][C:3]1[S:7][C:6]2=[N:8][C:9]([C:11]3[O:12][C:13]4[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH2:23][C:24]5[N:28]=[N:27][N:26]([C:29]6[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=6)[CH:25]=5)[C:14]=4[CH:15]=3)=[CH:10][N:5]2[N:4]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 69319AzidobenzeneHCID 23667548Sodium AscorbateHCID 867008962-Methoxy-6-(6-methoxy-4-(prop-2-yn-1-yloxy)benzofuran-2-yl)imidazo[2,1-b][1,3,4]thiadiazole

生成物 1

HCID 721933332-Methoxy-6-(6-methoxy-4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)benzofuran-2-yl)imidazo[2,1-b][1,3,4]thiadiazole収率 49%

試薬・触媒・溶媒 2

HCID 24463Copper sulfate pentahydrate触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 2-methoxy-6-(6-methoxy-4-(prop-2-yn-1-yloxy)benzofuran-2-yl)imidazo[2,1-b][1,3,4]thiadiazole (Example 9A, 20 mgs, 0.056 mmol) and azidobenzene (Example 9B, 19 mgs, 0.159 mmol) in DMF (4 mL, 51.7 mmol) was treated at r.t. and under a nitrogen atmosphere with sodium (R)-2-((S)-1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate (8 mgs, 0.040 mmol) and copper(II) sulfate pentahydrate (5 mgs, 0.020 mmol). The mixture was stirred for 2 hours (reaction followed by HPLC) and was then diluted with dichloromethane (60 mL) and washed with sat. NaHCO3, brine and dried (MgSO4). The solvent was evaporated and the solid residue was triturated with acetonitrile (2×1 mL) and lyophilized to give the title material (13 mgs, 0.027 mmol, 49% yield). LC (Method A): 2.213 min. HRMS (ESI) calcd for C23H19N6O4S [M+H]+ m/z 475.1183, found 475.1204. 1H NMR (DMSO-d6, 400 MHz) δ ppm: 9.04 (s, 1H), 8.37 (s, 1H), 7.90-7.99 (m, 2H), 7.58-7.67 (m, 2H), 7.51 (tt, J=7.4, 1.2 Hz, 1H), 6.97-7.03 (m, 1H), 6.83-6.88 (m, 1H), 6.71 (d, J=1.6 Hz, 1H), 5.38 (s, 3H), 4.20 (s, 3H), 3.83 (s, 3H).

後処理

  1. custom(reaction followed by HPLC)
  2. washwashed with sat. NaHCO3, brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated
  5. customthe solid residue was triturated with acetonitrile (2×1 mL)

出典と根拠

ORDレコード
ord-b63c7c2f3f2c4ac8b6f9129aa0eff699
出典データセット
uspto-grants-2016_04
特許番号
US09303065B2

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