Water → HCID 86691632, 화합물

HRID 624322노트

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HRID 624322 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([C:25]4[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([CH:34]=4)[C:30]([O:32]C)=[O:31])=[CH:18][C:11]=3[C:12]=2[C:13]2[NH:14][CH:15]=[CH:16][N:17]=2)=[CH:4][CH:3]=1.O.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([C:25]4[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([CH:34]=4)[C:30]([OH:32])=[O:31])=[CH:18][C:11]=3[C:12]=2[C:13]2[NH:17][CH:16]=[CH:15][N:14]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86691630methyl 5-(2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-6-nitrobenzofuran-5-yl)-2-methoxybenzoate

생성물 1

HCID 86691632HCID 86691632, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

To a mixture of methyl 5-(2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-6-nitrobenzofuran-5-yl)-2-methoxybenzoate (370 mg, 0.759 mmol) in a mixture of THF (40 mL)/water (4 mL) at room temperature was added a 2.0 M aqueous sodium hydroxide solution (1.518 mL, 3.04 mmol). The reaction mixture was heated to 50° C. and maintained at the same temperature overnight. The reaction mixture was concentrated to remove the solvent. The residue was diluted with water, acidified by using 1.5 N HCl, filtered and dried under suction to give the title compound as a yellow solid. Yield: 320 mg (89%). 1H NMR (400 MHz, DMSO-d6) δ ppm: 13.11-13.73 (m, 1H) 12.66-12.97 (m, 1H) 8.53 (s, 1H) 7.94-8.09 (m, 2H) 7.63-7.82 (m, 1H) 7.34-7.51 (m, 5H) 7.23 (d, J=8.78 Hz, 2H) 3.88 (s, 3H). LCMS: (ES+) m/z=474.23 (M+H)+; Column—ACQUITY UPLC BEH C8 (50×2.1 mm; 1.7 nm); Mphase A: 5 mM Ammonium Acetate:MeCN (95:5); Mphase B: 5 mM Ammonium Acetate:MeCN (5:95)

후처리

  1. temperaturemaintained at the same temperature overnight
  2. concentrationThe reaction mixture was concentrated
  3. customto remove the solvent
  4. additionThe residue was diluted with water
  5. filtrationfiltered
  6. customdried under suction

출처 및 근거

ORD 기록
ord-4102a28cac174df2a2d0b2417e3b26da
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303020B2

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