Hydrochloric Acid → 3-((4-(4-Amino-2-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

HRID 1878342노트

반응식

HRID 1878342 반응식
[C:1]([NH:5][C:6](=[O:32])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:31])[C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][C:22]=3[F:30])[CH2:16][CH2:15]2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].Cl>CC(O)C.[Fe]>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]([N:17]2[CH2:18][CH2:19][N:14]([CH2:13][C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:32])[CH2:15][CH2:16]2)=[O:31])=[C:22]([F:30])[CH:23]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 57917650N-tert-Butyl-3-((4-(2-fluoro-4-nitrobenzoyl)piperazin-1-yl)methyl)benzamide

생성물 1

HCID 579176473-((4-(4-Amino-2-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide수율 90.7%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 3776Isopropanol용매

실험 절차

To a suspension of iron (O) powder (3.3 g, 58.76 mmol) and N-tert butyl-3-((4-(2-fluoro-4-nitrobenzoyl)piperazin-1-yl)methyl)benzamide (2.6 g, 5.88 mmol) in propan-2-ol (75 mL) was added 1M aqueous hydrochloric acid (8.8 mL, 8.1 mmol). The reaction was stirred at room temperature for 2.5 hours, filtered through dicalite and concentrated under vacuum. The residue was dissolved in methanol and purified by strong cation exchange chromatography, eluting macroporous polystyrene sulfonic acid with 2M ammonia in methanol. The resulting solution was concentrated under vacuum to afford the title compound as a viscous orange oil (2.2 g).

후처리

  1. filtrationfiltered through dicalite
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in methanol
  4. custompurified by strong cation exchange chromatography
  5. washeluting macroporous polystyrene sulfonic acid with 2M ammonia in methanol
  6. concentrationThe resulting solution was concentrated under vacuum

출처 및 근거

ORD 기록
ord-4b05fec6881a42cbaef21bb572ced32c
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314091B2

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