Hydroxylamine → 9-(4-Fluorobenzyl)-N-Hydroxy-9h-Beta-Carboline-3-Carboxamide

HRID 722118

反応式

HRID 722118 の反応式
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([O:16]CC)=O)[N:2]=1.[H-].[Na+].[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1.[NH2:30][OH:31]>CN(C=O)C.CO.O>[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:12]2[C:13]3[CH:1]=[N:2][C:3]([C:14]([NH:30][OH:31])=[O:16])=[CH:4][C:5]=3[C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:24][CH:23]=1

参加物

8

反応物 4

HCID 787HydroxylamineHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 105078Ethyl Beta-Carboline-3-Carboxylate

生成物 1

HCID 30134599-(4-Fluorobenzyl)-N-Hydroxy-9h-Beta-Carboline-3-Carboxamide収率 39%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of ethyl 9H-β-carboline-3-carboxylate (368 mg, 1.53 mmol) in DMF (4 mL) under a nitrogen atmosphere was added NaH (61.2 mg, 60% in mineral oil, 1.53 mmol) portionwise, followed by 4-fluorobenzyl bromide (0.19 mL, 1.53 mmol). Stirring was continued for 24 hours at ambient temperature, water (10 mL) was then added to the mixture. The precipitate was filtered, washed with water and dried to give a solid that was dissolved in methanol (20 mL). To the resulting solution, H2NOH (20 mL, 50 wt. % solution in H2O, 0.30 mol) was added. The suspension was stirred for 5 days at ambient temperature. The mixture was then filtered, and the solid was boiled in methanol (40 mL). After filtration, the title product (0.20 g, 39%) was obtained. 1H NMR (300 MHz, DMSO-d6): δ 11.28 (1H, s), 9.02–9.08 (2H, m), 8.85 (1H, s), 8.48 (1H, d, J=9.0 Hz), 7.10–7.84 (7H, m), 5.85 (2H, s). HRMS (M+H)+ found: 336.1157. Calcd for C19H15N3O2F: 336.1148.

後処理

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried
  4. customto give a solid
  5. stirringThe suspension was stirred for 5 days at ambient temperature
  6. filtrationThe mixture was then filtered
  7. filtrationAfter filtration

出典と根拠

ORDレコード
ord-ab202bdd67744da588d578813329d47f
出典データセット
uspto-grants-2006_11
特許番号
US07138408B2

関連ノート

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