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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
ノート
印刷プレビュー

反応式

HRID 1727041 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran
溶媒
HCID 21584252Ethanol ethylacetate溶媒

反応条件

温度
20 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-380ba71b9e254d24af9b2cc1ec6a2ab1
出典データセット
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07495009B2

反応ノート

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