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Water → 1-{(1S,2R)-2-{[1-(4-Fluorophenyl)-1H-indazole-5-yl]oxy}-1-methyl-2-phenylethyl}-3-(2-furylmethyl)thiourea

HRID 1098888
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HRID 1098888 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C@H:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C@H:19]([CH3:21])[NH2:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH2:33][N:34]=[C:35]=[S:36].O>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C@H:18]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C@@H:19]([NH:20][C:35]([NH:34][CH2:33][C:29]4[O:28][CH:32]=[CH:31][CH:30]=4)=[S:36])[CH3:21])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 962WaterHCID 783802-(Isothiocyanatomethyl)furanHCID 59339817(alphaS,betaR)-beta-{[1-(4-Fluorophenyl)-1H-indazole-5-yl]oxy}-alpha-methylbenzeneethanamine

생성물 1

HCID 593398081-{(1S,2R)-2-{[1-(4-Fluorophenyl)-1H-indazole-5-yl]oxy}-1-methyl-2-phenylethyl}-3-(2-furylmethyl)thiourea수율 77.7%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

(αS,βR)-β-{[1-(4-Fluorophenyl)-1H-indazole-5-yl]oxy}-α-methylbenzeneethanamine (50 mg, 0.14 mmol), as described in Example 1, is dissolved in 0.89 mL dichloromethane and furylmethylisothiocyanate (19.3 mg, 0.14 mmol) is dropwise added. After stirring for 90 min at r.t. water (5 mL) is added and the reaction mixture extracted once with ethyl acetate (50 mL). The organic phase is washed with water (10 mL) and dried over Na2SO4. After filtration the solvent is removed and the residue purified by chromatography (silicagel, eluents: hexane/ethylacetate). 53.8 mg (77.7%) of the title compound are obtained.

후처리

  1. additionis added
  2. extractionthe reaction mixture extracted once with ethyl acetate (50 mL)
  3. washThe organic phase is washed with water (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration the solvent
  6. customis removed
  7. customthe residue purified by chromatography (silicagel, eluents: hexane/ethylacetate)

출처 및 근거

ORD 기록
ord-052fcd6439f94132a76ddbbe8031a8a4
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08143290B2

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