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

HRID 722118

반응식

HRID 722118 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ab202bdd67744da588d578813329d47f
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138408B2

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