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1-(4-Isothiocyanatophenyl)ethan-1-one → 1-(4-{[5-(butylamino)-3-(3-piperidin-1-ylpropyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino}phenyl)ethanone

HRID 1727041
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인쇄 미리보기

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HRID 1727041 반응식
[CH2:1]([NH:5][C:6]1[N:11]=[C:10]([NH:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:9]([N+:22]([O-])=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[C:25]([C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=S)=[CH:30][CH:29]=1)(=[O:27])[CH3:26]>C(OCC)(=O)C.C(O)C.[Pd].O1CCCC1>[CH2:1]([NH:5][C:6]1[N:11]=[C:10]2[N:12]([CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:35]([NH:34][C:31]3[CH:32]=[CH:33][C:28]([C:25](=[O:27])[CH3:26])=[CH:29][CH:30]=3)=[N:22][C:9]2=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]
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참가 물질

6

반응물 2

HCID 2427791-(4-Isothiocyanatophenyl)ethan-1-oneHCID 86606889N6-butyl-3-nitro-N2-(3-piperidin-1-ylpropyl)pyridine-2,6-diamine

생성물 1

HCID 575662601-(4-{[5-(butylamino)-3-(3-piperidin-1-ylpropyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino}phenyl)ethanone수율 34.4%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran
용매
HCID 21584252Ethanol ethylacetate용매

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온도
20 °C

실험 절차

N6-butyl-3-nitro-N2-(3-piperidin-1-ylpropyl)pyridine-2,6-diamine (500 mg) in solution in a mixture of ethyl acetate/ethanol 3:1 (10 ml), and 10% palladium on carbon (50 mg) are introduced into an autoclave. After stirring for 3 hours under a hydrogen atmosphere (3 bar) at a temperature of approximately 20° C., the mixture is filtered on celite in a flask containing a solution of 4-acetylphenyl-isothiocyanate (270 mg, 1 eq) in tetrahydrofuran (10 ml). N-cyclohexylcarbodiimide-N-methyl-polystyrene resin (acquired from Novabiochem; load 1.9 mmol/g; 2.63 g, 3 eq) is added to the filtrate thus obtained. The mixture is heated to reflux for 15 hours, cooled down to ambient temperature then filtered on frit and the filtrate is concentrated under reduced pressure at 40° C. Purification of the residue by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 9:1) produces the expected compound (230 mg; 34% yield).

후처리

  1. additionare introduced into an autoclave
  2. filtrationthe mixture is filtered on celite in a flask
  3. customthus obtained
  4. temperatureThe mixture is heated
  5. temperatureto reflux for 15 hours
  6. temperaturecooled down to ambient temperature
  7. filtrationthen filtered on frit
  8. concentrationthe filtrate is concentrated under reduced pressure at 40° C
  9. customPurification of the residue by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 9:1)

출처 및 근거

ORD 기록
ord-380ba71b9e254d24af9b2cc1ec6a2ab1
출처 데이터셋
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07495009B2

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