3-[5-Allyl-4-(4-methoxy-phenyl)-thiazol-2-ylmethoxy]-2,6-difluoro-benzamide → 2,6-Difluoro-3-[4-(4-methoxy-phenyl)-5-propyl-thiazol-2-ylmethoxy]-benzamide

HRID 538511노트

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HRID 538511 반응식
[CH2:1]([C:4]1[S:8][C:7]([CH2:9][O:10][C:11]2[C:12]([F:21])=[C:13]([C:17]([F:20])=[CH:18][CH:19]=2)[C:14]([NH2:16])=[O:15])=[N:6][C:5]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH:2]=[CH2:3]>CO>[F:21][C:12]1[C:11]([O:10][CH2:9][C:7]2[S:8][C:4]([CH2:1][CH2:2][CH3:3])=[C:5]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:6]=2)=[CH:19][CH:18]=[C:17]([F:20])[C:13]=1[C:14]([NH2:16])=[O:15]

참가 물질

3

반응물 1

HCID 594026523-[5-Allyl-4-(4-methoxy-phenyl)-thiazol-2-ylmethoxy]-2,6-difluoro-benzamide

생성물 1

HCID 594027972,6-Difluoro-3-[4-(4-methoxy-phenyl)-5-propyl-thiazol-2-ylmethoxy]-benzamide수율 239%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
25 °C

실험 절차

To a solution of 3-[5-allyl-4-(4-methoxy-phenyl)-thiazol-2-ylmethoxy]-2,6-difluoro-benzamide (0.1 g, 0.02 mmol) in 5 ml of anhydrous methanol was added dry 50 mg of dry Pd—C. The reaction mixture was stirred at 25° C. for 12 h under hydrogen atmosphere. The reaction mixture was filtered over the bed of celite. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by column chromatography on silica (230-400μ) using ethyl acetate/hexane (50:50) as the eluent to provide the title compound as white solid (0.02 g, 2%). 1H NMR (DMSO-d6, 400 MHz); δ 0.92 (t, 3H, J=7.2 Hz), 1.63-1.65 (m, 2H), 2.8 (t, 2H, J=7.6 Hz (o-coupling), 3.79 (s, 3H), 5.47 (s, 2H), 7.02 (d, 2H, J=8.8 Hz (o-coupling), 7.11 (m, 1H), 7.42 (m, 1H), 7.53 (d, 2H, J=8.8 Hz (o-coupling), 7.88 (s, 1H), 8.16 (s, 1H), 8.38 (d, 1H, J=8.4 Hz (O-coupling). MS ES+ (419.14), HPLC (method 5) Rt=16.58 min.

후처리

  1. dry with materialdry 50 mg of dry Pd—C
  2. filtrationThe reaction mixture was filtered over the bed of celite
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. customthe residue was purified by column chromatography on silica (230-400μ)

출처 및 근거

ORD 기록
ord-3e450e2e09714a7d91b08323795eccbb
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865736B2

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