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Pyridine → 3-methyl-6-(morpholin-4-yl)-2-{2-oxo-2-[4-(trifluoromethyl)-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one

HRID 2278614
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HRID 2278614 반응식
N1C=CC=CC=1.[F:7][C:8]([F:19])([F:18])[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][NH:13]2.Cl.CN(C)CCCN=C=NCC.[CH3:32][N:33]1[C:38](=[O:39])[CH:37]=[C:36]([N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)[N:35]=[C:34]1[CH2:46][C:47]([O-])=[O:48].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[CH3:32][N:33]1[C:38](=[O:39])[CH:37]=[C:36]([N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)[N:35]=[C:34]1[CH2:46][C:47](=[O:48])[N:13]1[C:14]2[C:10](=[C:9]([C:8]([F:7])([F:18])[F:19])[CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:12]1
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참가 물질

8

반응물 4

HCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 162444454-(Trifluoromethyl)indolineHCID 57523684Sodium [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate

생성물 1

HCID 573895513-methyl-6-(morpholin-4-yl)-2-{2-oxo-2-[4-(trifluoromethyl)-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one
수율 30.2%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

3 ml of pyridine, 94 mg of 4-trifluoromethyl-2,3-dihydro-1H-indole and 153 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are successively added to a solution of 138 mg of sodium [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate in 3 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 16 hours. After the addition of 50 ml of water and extraction with ethyl acetate (3×15 ml), the organic phases are combined and then washed with water (2×15 ml), and a saturated aqueous sodium chloride solution (15 ml), and then dried over magnesium sulfate, filtered through sintered glass, and concentrated under reduced pressure. The solid obtained is washed with diethyl ether (5 ml) and then dried, so as to give 64 mg of 3-methyl-6-(morpholin-4-yl)-2-{2-oxo-2-[4-(trifluoromethyl)-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one in the form of a pink solid, the characteristics of which are the following:

후처리

  1. washwashed with water (2×15 ml)
  2. dry with materiala saturated aqueous sodium chloride solution (15 ml), and then dried over magnesium sulfate
  3. filtrationfiltered through sintered glass
  4. concentrationconcentrated under reduced pressure
  5. customThe solid obtained
  6. washis washed with diethyl ether (5 ml)
  7. customdried

출처 및 근거

ORD 기록
ord-c7d7c19ed6c04fbb8066f0b74fc57d62
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133168B2

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