2-{3-[2,2-Difluoro-2-(4-fluoronaphthyl)acetylamino]-2-fluoro-6-nitrophenyl]ethyl Acetate → 2-[2-Amino-5-[2,2-difluoro-2-(4-fluoronaphthyl)acetylamino]-6-fluorophenyl}ethyl Acetate

HRID 1060221노트

반응식

HRID 1060221 반응식
[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[C:9]([NH:16][C:17](=[O:32])[C:18]([F:31])([F:30])[C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([F:29])=[CH:21][CH:20]=2)[C:8]=1[F:33])(=[O:3])[CH3:2]>C(O)C.C1COCC1.[Pd]>[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:8]([F:33])=[C:9]([NH:16][C:17](=[O:32])[C:18]([F:30])([F:31])[C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([F:29])=[CH:21][CH:20]=2)[CH:10]=[CH:11][C:12]=1[NH2:13])(=[O:3])[CH3:2]

참가 물질

5

반응물 1

HCID 224753272-{3-[2,2-Difluoro-2-(4-fluoronaphthyl)acetylamino]-2-fluoro-6-nitrophenyl]ethyl Acetate

생성물 1

HCID 224753342-[2-Amino-5-[2,2-difluoro-2-(4-fluoronaphthyl)acetylamino]-6-fluorophenyl}ethyl Acetate수율 83.3%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 2-{3-[2,2-difluoro-2-(4-fluoronaphthyl)acetylamino]-2-fluoro-6-nitrophenyl}ethyl acetate (4.9 g, 10.5 mmol), as prepared in the preceding step, and Pd/C (10%, 500 mg) in ethanol (50 mL) and THF (50 mL) was stirred under hydrogen for 5 hours. The reaction mixture was filtered through Celite, and washed with THF and MeOH. The filtrate and washings were combined, concentrated in vacuo, and flash chromatographed on silica gel eluting with EtOAc/DCM (0 to 2%) to produce the title compound (3.8 g, 83%) as an off white solid. 1H-NMR (400 MHz, CDCl3) δ 8.27 (d, J=8.2 Hz, 1H), 8.19 (d, J=8.6 Hz, 1H), 8.10 (s, 1H), 7.82 (m, 2H), 7.63 (m, 2H), 7.19 (t, J=8.6 Hz, 1H), 6.46 (d, J=8.7 Hz, 1H), 4.19 (t, J=7.4 Hz, 2H), 4.08 (s, 2H), 2.91(t, J=7.3 Hz, 2H), 2.08 (s, 3H).

후처리

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with THF and MeOH
  3. concentrationconcentrated in vacuo, and flash
  4. customchromatographed on silica gel eluting with EtOAc/DCM (0 to 2%)

출처 및 근거

ORD 기록
ord-fdede8ac61a54c7cb83ffa5f470bb546
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521663B2

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