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Hydrochloric Acid → HCID 135483507, 화합물

HRID 2377975
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HRID 2377975 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12](O)[C:11]([C:14]3[C:15](=[O:31])[NH:16][CH:17]=[CH:18][C:19]=3[NH:20][CH2:21][CH:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[OH:23])=[N:10][CH:9]=2)=[CH:4][CH:3]=1.Cl>CO.[Cl-].[Ti+3].[Cl-].[Cl-]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:14]3[C:15](=[O:31])[NH:16][CH:17]=[CH:18][C:19]=3[NH:20][CH2:21][CH:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[OH:23])=[N:10][CH:9]=2)=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 136331968HCID 136331968, 화합물

생성물 1

HCID 135483507HCID 135483507, 화합물수율 41.2%

시약·촉매·용매 2

HCID 10313229titanium(III) trichloride촉매HCID 887Methanol용매

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온도
65 °C

실험 절차

To a stirred solution of 3-[5-(4-bromo-phenyl)-1-hydroxy-1H-imidazol-2-yl]-4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-1H-pyridin-2-one (0.015 g, 0.030 mmol) in methanol (4 mL) was treated with titanium(III) chloride ((9.25 wt % in 27.4 wt % hydrochloric acid, ˜200 μL). The reaction was heated at 65° C. for 1 hour, then quenched with water and the solvents were evaporated. The residue was purified by Prep HPLC (ammonium acetate/acetonitrile/water) to give the title material (0.006 g, 41%) as a beige solid. HPLC 100% (220 nm), LCMS (+ESI, M+H+) m/z 485,487, (−ESI, M−H−) m/z 483, 485; 1H NMR (400 MHz, methanol-d4) δ (ppm): 3.64 (1H, dd, J=13.3 and 7.1 Hz), 3.74 (1H, dd, J=13.3 and 4.5 Hz), 5.03 (1H, m), 6.26 (1H, d, J=7.5 Hz), 7.23-7.56 (9H, m), 7.77 (1H, d, J=8.6 Hz).

후처리

  1. customquenched with water
  2. customthe solvents were evaporated
  3. customThe residue was purified by Prep HPLC (ammonium acetate/acetonitrile/water)

출처 및 근거

ORD 기록
ord-6f98d53d4819489083fccb151e4ac8ff
출처 데이터셋
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07470713B2

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