Tetrahydrofuran → 6-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-1,4-dihydro-quinoxaline-2,3-dione

HRID 642883ノート

反応式

HRID 642883 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[C:19]([N:20]4[CH2:25][CH2:24][N:23]([CH2:26][C:27]5[CH:28]=[C:29]([NH2:34])[C:30]([NH2:33])=[CH:31][CH:32]=5)[CH2:22][CH2:21]4)[C:13]=3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O1CCCC1.[C:40](N1C=CN=C1)(=[O:48])[C:41](N1C=CN=C1)=[O:42]>C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[C:19]([N:20]4[CH2:21][CH2:22][N:23]([CH2:26][C:27]5[CH:28]=[C:29]6[C:30](=[CH:31][CH:32]=5)[NH:33][C:41](=[O:42])[C:40](=[O:48])[NH:34]6)[CH2:24][CH2:25]4)[C:13]=3[N:12]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 1004391,1'-OxalyldiimidazoleHCID 58592820HCID 58592820、化合物

生成物 1

HCID 445934246-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-1,4-dihydro-quinoxaline-2,3-dione収率 24.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

In a round bottom flask under nitrogen was combined 4-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-benzene-1,2-diamine (0.17 g, 0.37 mMol), tetrahydrofuran (20 mL), and 1,1′-oxalyldiimidazole (0.284 g, 1.5 mMol) and the solution stirred overnight. Upon arrival the solution was diluted with ethyl acetate (100 mL) and washed with water (100 mL). A precipitate forms and was collected by filtration. The organic layer was concentrated to dryness on a rotary evaporator and combined with the precipitate. Purification by RP-HPLC (Method E) yielded 46 mg (24% yield) of 6-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-1,4-dihydro-quinoxaline-2,3-dione as an off-white solid. 1H NMR (DMSO-d6): δ=12.19 (s, 1H), 12.09 (s, 1H), 9.82 (br s, 1H), 8.07 (d, 2H, J=8.6 Hz), 7.58 (d, 2H, J=8.6 Hz), 7.27 (m, 2H), 7.22 (d ,1H, J=8.6 Hz), 7.13 (m, 2H), 6.64 (m, 1H), 4.48 (br s, 2H), 4.44 (s, 2H), 3.50 (br s, 2H), 3.38 (br s, 2H), 3.09 (m, 2H), 1.34 (s, 9H). HPLC: Xterra MS C18, 3.5 μm, 4.6×50 mm, flow=0.8 m/min, 5-95% ACN/PICB6 over 10 mins., rt=5.840 mins., 79% pure @ 210 nm, 77% pure @ 300 nm. LC/MS (Method A), rt=1.05 mins., purity=79.19%, calculated mass=508, [M+H]+=509, [M−H]−=507.

後処理

  1. customIn a round bottom flask under nitrogen was combined
  2. washwashed with water (100 mL)
  3. filtrationA precipitate forms and was collected by filtration
  4. concentrationThe organic layer was concentrated to dryness on a rotary evaporator
  5. customPurification by RP-HPLC (Method E)

出典と根拠

ORDレコード
ord-8606f4d0ecd745adb48a1063849204b9
出典データセット
uspto-grants-2010_04
特許番号
US07696210B2

反応ノート

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