5-Nitro-2-Furoic Acid → 1-(9H-carbazol-4-yloxy)-3-{4-(5-nitro-2-furoyl)piperazin-1-yl}propan-2-ol

HRID 507337

反応式

HRID 507337 の反応式
[N+:1]([C:4]1[O:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:42]1[C:54]2[NH:53][C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]=2[C:45]([O:55][CH2:56][CH:57]([OH:65])[CH2:58][N:59]2[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]2)=[CH:44][CH:43]=1>CN(C=O)C.C(Cl)Cl>[CH:42]1[C:54]2[NH:53][C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]=2[C:45]([O:55][CH2:56][CH:57]([OH:65])[CH2:58][N:59]2[CH2:64][CH2:63][N:62]([C:9]([C:7]3[O:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[O:11])[CH2:61][CH2:60]2)=[CH:44][CH:43]=1

参加物

8

反応物 5

HCID 125775-Nitro-2-Furoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 16730483HCID 16730483、化合物

生成物 1

HCID 167308091-(9H-carbazol-4-yloxy)-3-{4-(5-nitro-2-furoyl)piperazin-1-yl}propan-2-ol収率 51%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-Nitrofuroic acid (1.56 g, 9.9 mmol) in DMF (30 mL) was added DIPEA (4.3 mL, 24.8 mmol), EDCI (3.18 g, 16.5 mmol), HOBt (0.44 g, 3.3 mmol) followed by the 1-(9H-carbazol-4-yloxy)-3-piperazin-1-ylpropan-2-ol (2.7 g, 8.3 mmol, prepared following the procedure described above in step 11, example 26). The reaction mixture was stirred at room temperature for 12 hours and was diluted with DCM (100 mL), washed with water and brine solution. The organic layer was dried on anhydrous Na2SO4, concentrated and purified by silica gel column chromatography, using hexane/EtOAc (4:6) to afford the title compound as yellow colored solid (2.0 g, 51% yield) with m.p: 178-181° C. 1H NMR (400 MHz, DMSO): δ 2.30-2.60 (m, 4H), 2.67-2.69 (m, 2H), 3.63-3.69 (m, 4H), 4.13-4.21 (m, 3H), 5.08 (s, 1H), 6.69 (d, 1H, J=8.0 Hz), 7.06 (d, 1H, J=8.0 Hz), 7.14 (t, 1H, J=8.0 Hz), 7.24-7.36 (m, 3H), 7.44 (d, 1H, J=8.0 Hz), 7.66 (d, 1H, J=4.0 Hz), 8.22 (d, 1H, 8.0 Hz), and 11.25 (s, 1H). MS m/z: 464.8 (M+1).

後処理

  1. customprepared
  2. washwashed with water and brine solution
  3. dry with materialThe organic layer was dried on anhydrous Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-b1f89fd6d798400ab29c3f617f4af488
出典データセット
uspto-grants-2010_08
特許番号
US07786142B2

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