Triethylamine → [4-[(R)-3-(2,4-dimethyl-phenoxy)-2-hydroxy-propylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione

HRID 561910ノート

反応式

HRID 561910 の反応式
Cl.IC1C=CNC(=O)C=1[C:10]1[NH:11][C:12]2[C:20]([N:21]=1)=[C:19]([CH3:22])[C:18]1[C:17](=[O:23])[N:16]([CH:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)[C:15](=[O:31])[C:14]=1[CH:13]=2.Cl.Cl[C:34]1[CH:39]=[CH:38][NH:37][C:36](=[O:40])[C:35]=1C1NC2C(N=1)=C(C)C1C(=O)N(C3CCN(C)CC3)C(=O)C=1C=2.[NH2:63][CH2:64][C@@H:65]([OH:76])[CH2:66][O:67][C:68]1[CH:73]=[CH:72][C:71]([CH3:74])=[CH:70][C:69]=1[CH3:75].CCN(CC)CC>CCO>[CH3:75][C:69]1[CH:70]=[C:71]([CH3:74])[CH:72]=[CH:73][C:68]=1[O:67][CH2:66][C@H:65]([OH:76])[CH2:64][NH:63][C:34]1[CH:39]=[CH:38][NH:37][C:36](=[O:40])[C:35]=1[N:11]1[C:12]2[C:20](=[C:19]([CH3:22])[C:18]3[C:17](=[O:23])[N:16]([CH:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[C:15](=[O:31])[C:14]=3[CH:13]=2)[N:21]=[CH:10]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 2133977(2R)-1-amino-3-(2,4-dimethylphenoxy)propan-2-olHCID 1363510992-(4-Chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione HydrochlorideHCID 1363511752-(4-Iodo-2-oxo-1,2-dihydro-pyridin-3-yl)-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione Hydrochloride

生成物 1

HCID 86621613[4-[(R)-3-(2,4-dimethyl-phenoxy)-2-hydroxy-propylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione収率 57%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a suspension of 2-(4-Iodo-2-oxo-1,2-dihydro-pyridin-3-yl)-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione Hydrochloride and 2-(4-Chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione Hydrochloride (0.75 g, 1.45 mmol), (R)-3-amino-1-(2,4-dimethylphenoxy)-2-propanol (0.34 g, 1.73 mmol) in EtOH (20 mL) was added Et3N (0.61 mL, 4.35 mmol) and the resulting mixture was heated at reflux for overnight. The reaction mixture was evaporated in vacuo and the residue was purified by flash chromatography (10% (6% NH3/MeOH)/CHCl3) to afford 2-{[4-[(R)-3-(2,4-dimethyl-phenoxy)-2-hydroxy-propylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione (0.45 g, 57%) as a yellow solid.

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for overnight
  3. customThe reaction mixture was evaporated in vacuo
  4. customthe residue was purified by flash chromatography (10% (6% NH3/MeOH)/CHCl3)

出典と根拠

ORDレコード
ord-8b4581482e894a888781ad76207dc737
出典データセット
uspto-grants-2011_11
特許番号
US08063225B2

反応ノート

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