Ethanethiol → 2,8-Dihydroxy-5-[4-[2-(1-piperidinyl)ethoxy]phenyl]-6H-benzo[c]phenanthridine

HRID 1711

反応式

HRID 1711 の反応式
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:19]3[N:18]([C:20]4[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]5[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]5)=[CH:22][CH:21]=4)[CH2:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([O:35]C)[CH:15]=4)[C:10]=3[CH:9]=[CH:8][C:7]=2[CH:37]=1.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:19]3[N:18]([C:20]4[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][N:29]5[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]5)=[CH:24][CH:25]=4)[CH2:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([OH:35])[CH:15]=4)[C:10]=3[CH:9]=[CH:8][C:7]=2[CH:37]=1

参加物

5

反応物 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 109180382,8-Dimethoxy-5-[4-[2-(1-piperidinyl)ethoxy]phenyl]-6H-benzo[c]phenanthridine

生成物 1

HCID 104122492,8-Dihydroxy-5-[4-[2-(1-piperidinyl)ethoxy]phenyl]-6H-benzo[c]phenanthridine収率 60.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of the product of Example 13 (195 mg, 0.39 mmol) in methylene chloride (25 mL) was treated with ethanethiol (200 mg, 220 mL, 3.2 mmol) and aluminum chloride (320 mg, 2.4 mmol). After stirring for 4 h at ambient temperature, the mixture was quenched carefully with THF (25 mL) and saturated sodium bicarbonate (25 mL). The layers were separated, the aqueous layer was extracted with THF (25 mL), and the combined organic layers were dried (sodium sulfate) and concentrated. The residue was purified by radial chromatography (silica gel, 1:1 hexane:ethyl acetate, 10-20% methanol, under an ammonia atmosphere) to provide 110 mg (60%) of the title compound as a tan foam. An analytical sample was crystallized from methanol as a light red solid: 1H NMR (300 MHz, dimethylformamide-d7) d 9.92 (br s, 1H), 9.74 (br s, 1H), 7.99 (d, J=8.8 Hz, 1H), 7.78 (d, J=8.5 Hz, 1H), 7.69 (d, J=9.0 Hz, 1H), 7.63 (d, J=8.7 Hz, 1H), 7.23 (d, J=2.0 Hz, 1H), 6.98 (dd, J=9.0, 2.1 Hz, 1H), 6.84 (dd, J=8.4, 2.1 Hz, 1H), 6.73 (m, 5H), 3.92 (t, J=5.9 Hz, 2H), 2.57 (t, J=5.9 Hz, 2H), 2.38 (m, 4H), 1.4-1.5 (m, 4H), 1.3-1.4 (m, 2H); IR (KBr) 3560, 3490 cm-1 ; MS (FD+) m/e 466 (M+); Anal. calc'd. for C30 H30N2O3.0.5H2O: C, 75.75; H, 6.58; N, 5.89. Found: C, 75.82; H, 6.76; N, 5.95.

後処理

  1. customthe mixture was quenched carefully with THF (25 mL) and saturated sodium bicarbonate (25 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with THF (25 mL)
  4. dry with materialthe combined organic layers were dried (sodium sulfate)
  5. concentrationconcentrated
  6. customThe residue was purified by radial chromatography (silica gel, 1:1 hexane

出典と根拠

ORDレコード
ord-3b73803622b24e07932df49f9cb1154a
出典データセット
uspto-grants-1998_03
特許番号
US05726186

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