N-methyl-2-pyrrolidone → 1-{6-[2-(2,4-Dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-piperidine-4-carboxylic acid methyl ester

HRID 216269

반응식

HRID 216269 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[C:15](Cl)[N:14]=[C:13]([O:18][CH3:19])[N:12]=2)[CH2:7][CH2:6]1)=[O:4].[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[CH2:28][CH2:29][NH2:30].C(=O)(O)[O-].[Na+].CN1CCCC1=O>O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[C:15]([NH:30][CH2:29][CH2:28][C:22]3[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=3[Cl:20])[N:14]=[C:13]([O:18][CH3:19])[N:12]=2)[CH2:7][CH2:6]1)=[O:4]

참가 물질

6

반응물 4

HCID 13387N-methyl-2-pyrrolidoneHCID 1429382,4-Dichlorophenethylamine2회HCID 516892Sodium BicarbonateHCID 866157151-(6-Chloro-2-methoxy-pyrimidin-4-yl)-piperidine-4-carboxylic acid methyl ester

생성물 1

HCID 690694161-{6-[2-(2,4-Dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-piperidine-4-carboxylic acid methyl ester수율 44.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
140 °C

실험 절차

In a tube is combined 1-(6-chloro-2-methoxy-pyrimidin-4-yl)-piperidine-4-carboxylic acid methyl ester [103 mg, 0.36 mmol], 2-(2,4-dichloro-phenyl)-ethylamine (0.163 mL, 1.08 mmol), sodium bicarbonate (181 mg, 2.16 mmol) and N-methylpyrrolidinone (2 mL). The mixture is heated at 140° C. for 12 h. Additional 2-(2,4-dichloro-phenyl)-ethylamine (0.2 mL, 1.33 mmol) is added and heating at 140° C. is continued for another 12 h. The mixture is diluted with water (30 mL) and extracted twice with EtOAc (30 mL). The organic extracts are washed twice with water (40 mL) and once with brine (30 mL), combined, dried over magnesium sulfate, filtered and concentrated. The residue is subjected to chromatography on silica gel eluting with 40% ethyl acetate:heptane to afford 1-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-piperidine-4-carboxylic acid methyl ester [70 mg, 44%] as a solid.

후처리

  1. customIn a tube is combined
  2. temperatureheating at 140° C.
  3. extractionextracted twice with EtOAc (30 mL)
  4. washThe organic extracts are washed twice with water (40 mL) and once with brine (30 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-247c3aba7db44a629a0d1f8a468a55a0
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193183B2

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