Hydrochloric Acid → ethyl 3-{4-[(4-{[3-tert-butyl-5-(2-phenylethyl)-1H-pyrazol-1-yl]methyl}benzyl)oxy]-2-fluorophenyl}propanoate

HRID 2110910노트

반응식

HRID 2110910 반응식
[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:21][C:22]1[CH:43]=[CH:42][C:25]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:30]([F:41])[CH:29]=2)=[CH:24][CH:23]=1.Cl>CN(C)C=O>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:7]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:30]([F:41])[CH:29]=3)=[CH:42][CH:43]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 23143241Ethyl 3-(4-([4-(chloromethyl)benzyl]oxy}-2-fluorophenyl)propanoateHCID 231573073-tert-butyl-5-(2-phenylethyl)-1H-pyrazole

생성물 1

HCID 23159843ethyl 3-{4-[(4-{[3-tert-butyl-5-(2-phenylethyl)-1H-pyrazol-1-yl]methyl}benzyl)oxy]-2-fluorophenyl}propanoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-tert-butyl-5-(2-phenylethyl)-1H-pyrazole (250 mg, 1.1 mmol) in N,N-dimethylformamide (5 mL) was added sodium hydride (60% in oil, 40 mg, 1.0 mmol) at 0° C., and the mixture was allowed to warm to room temperature and stirred for 30 min. Ethyl 3-(4-{[4-(chloromethyl)benzyl]oxy}-2-fluorophenyl)propanoate (350 mg, 1.0 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into 1 N hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (Manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1-1:1) to give the title compound as a yellow oil. 1H NMR (CDCl3) δ: 1.22 (3H, t, J=7.2 Hz), 1.33 (9H, s), 2.57 (2H, t, J=7.6 Hz), 2.68-2.76 (2H, m), 2.78-2.83 (2H, m), 2.89 (2H, t, J=7.7 Hz), 4.11 (2H, q, J=7.2 Hz), 4.97 (2H, s), 5.21 (2H, s), 5.98 (1H, s), 6.60-6.69 (2H, m), 6.99-7.12 (5H, m), 7.16-7.30 (3H, m), 7.32 (2H, d, J=8.1 Hz).

후처리

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1-1:1)

출처 및 근거

ORD 기록
ord-0343cf098d684f56a643c692d76c771c
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517910B2

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