Quinoline → HCID 86749395、化合物

HRID 1720436

反応式

HRID 1720436 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[S:13][C:12]([C:14]#[C:15][C@H:16]([N:18]([OH:22])[C:19]([NH2:21])=[O:20])[CH3:17])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.N1C2C(=CC=CC=2)C=CC=1>CC(C)=O.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[S:13][C:12](/[CH:14]=[CH:15]\[C@H:16]([N:18]([OH:22])[C:19]([NH2:21])=[O:20])[CH3:17])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 7047QuinolineHCID 3086671Atreleuton

生成物 1

HCID 86749395HCID 86749395、化合物収率 29%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 180Acetone溶媒

実験手順

A solution of (R)-N-{3-[5-(4-fluorophenylmethyl)thien-2-yl]-1-methyl-2-propynyl}-N-hydroxyurea (0.50 g, 1.57 mmol), prepared as in step 4, quinoline (0.25 mL, 2.11 mmol), and 5% palladium on calcium chloride poisoned with lead (0.025 g) in acetone (15 mL) was allowed to stir under hydrogen (atmospheric pressure) for 24 hours. The solution was filtered through celite and solvents removed in vacuo. The resulting oil was taken up in ethyl acetate (50mL) and washed with aqueous 1M H3PO4 (3×25 mL) and aqueous NaHCO3 (3×25 mL). The solution was dried (MgSO4) after which the solvent was evaporated to yield a yellow oil. The residue was purified by chromatography on silica gel (50% ethyl acetate/hexane/1% acetic acid). The resulting solid was crystallized from hot ethyl acetate/hexane to yield 0.145g (29%) of Z-N-[3-(5-(4-Fluorophenylmethyl)-thien-2-yl)-1-[R]-methyl-2-propenyl]-N-hydroxyurea. m.p. 123°-4° C., MS. (DCI/NH3) m/e 321 (M+H)+, 338 (M+NH4)+. 1H NMR (DMSO-d6, 300 MHz) δ1.16 (d,J=6.3 Hz, 3H), 4.1 (s, 2H), 5.25 (m, 1H), 5.67 (rid, J=9.0, 11.7 Hz, 1H), 6.35 (s, 2H), 6.43 (d, J=11.7 Hz, 1H), 6.83 (d, J=3.6 Hz, 1H), 6.94 (d, J=3.6 Hz, 1H), 7.13 (m, 2H), 7.32 (m, 2H), 9.18 (s, 1H). Anal calcd for C17H17FN2O2S: C, 59.98; H, 5.35; N, 8.74. Found C, 59.79; H, 5.25; N, 8.71.

後処理

  1. filtrationThe solution was filtered through celite and solvents
  2. customremoved in vacuo
  3. washwashed with aqueous 1M H3PO4 (3×25 mL) and aqueous NaHCO3 (3×25 mL)
  4. dry with materialThe solution was dried (MgSO4) after which the solvent
  5. customwas evaporated
  6. customto yield a yellow oil
  7. customThe residue was purified by chromatography on silica gel (50% ethyl acetate/hexane/1% acetic acid)
  8. customThe resulting solid was crystallized from hot ethyl acetate/hexane

出典と根拠

ORDレコード
ord-de67acdf47834dcc89d92a3044ffdb3b
出典データセット
uspto-grants-1996_04
特許番号
US05506261

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