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Water → N-Phenyl-N'-(4-(6-(3,4,5-trimethoxyphenylamino)pyrimidin-4-yloxy)phenyl)urea hydrochloride

HRID 1433662
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HRID 1433662 반응식
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:17])=[CH:11][CH:10]=2)[CH:3]=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:31]=[C:32]([O:36][CH3:37])[C:33]=1[O:34][CH3:35])[NH2:30].C(OCC)(=O)C.O>CN1CCCC1=O.CCCCCC>[ClH:1].[C:19]1([NH:18][C:16]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][C:4]3[CH:3]=[C:2]([NH:30][C:29]4[CH:31]=[C:32]([O:36][CH3:37])[C:33]([O:34][CH3:35])=[C:27]([O:26][CH3:25])[CH:28]=4)[N:7]=[CH:6][N:5]=3)=[CH:10][CH:11]=2)=[O:17])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
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참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl Acetate2회HCID 322853,4,5-TrimethoxyanilineHCID 22937019N-(4-(6-Chloropyrimidin-4-yloxy)phenyl)-N'-phenylurea

생성물 1

HCID 22936469N-Phenyl-N'-(4-(6-(3,4,5-trimethoxyphenylamino)pyrimidin-4-yloxy)phenyl)urea hydrochloride수율 48%

시약·촉매·용매 2

HCID 8058
Hexane
용매
HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

N-(4-(6-Chloropyrimidin-4-yloxy)phenyl)-N′-phenyl urea (68.0 mg, 0.200 mmol) and 3,4,5-trimethoxyaniline (183 mg, 1.00 mmol) were heated and stirred in 1-methylpyrrolidone (1 ml) at 150° C. for 2 hours. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with saturated aqueous sodium bicarbonate, water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent—ethyl acetate:hexane=3:1), the fraction containing the target substance was concentrated, converted to a hydrochloride with 1N hydrochloric acid and suspended in methanol, the suspension was diluted with ethyl acetate and the crystals were filtered out, washed with ethyl acetate and blow-dried to obtain the title compound (50.0 mg, 0.095 mmol, 48%) as light green crystals.

후처리

  1. washthe organic layer was washed with saturated aqueous sodium bicarbonate, water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered off
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. additionthe fraction containing the target substance
  7. concentrationwas concentrated
  8. additionthe suspension was diluted with ethyl acetate
  9. filtrationthe crystals were filtered out
  10. washwashed with ethyl acetate
  11. customblow-dried

출처 및 근거

ORD 기록
ord-a14419bd8c754a5b9f99a759b2b4fcea
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07612092B2

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