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 561910노트

반응식

HRID 561910 반응식
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

참가 물질

6

반응물 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

생성물 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-dione수율 57%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8b4581482e894a888781ad76207dc737
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063225B2

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