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

HRID 2278636
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HRID 2278636 반응식
N1C=CC=CC=1.[N:7]1([C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][CH2:16][NH:17]3)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.Cl.CN(C)CCCN=C=NCC.[N:34]1([C:40]2[N:41]=[C:42]([CH2:47][C:48]([O-])=[O:49])[NH:43][C:44](=[O:46])[CH:45]=2)[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[N:34]1([C:40]2[N:41]=[C:42]([CH2:47][C:48]([N:17]3[C:18]4[C:14](=[C:13]([N:7]5[CH2:8][CH2:9][O:10][CH2:11][CH2:12]5)[CH:21]=[CH:20][CH:19]=4)[CH2:15][CH2:16]3)=[O:49])[NH:43][C:44](=[O:46])[CH:45]=2)[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1
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참가 물질

8

반응물 4

HCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86699280HCID 86699280, 화합물HCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

생성물 1

HCID 1361964546-(morpholin-4-yl)-2-{2-[4-(morpholin-4-yl)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}pyrimidin-4(3H)-one

시약·촉매·용매

3
HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

8 ml of pyridine, 200 mg of 4-morpholin-4-yl-2,3-dihydro-1H-indole (prepared using 4-bromoindoline as described in WO2007103370) and 330 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are successively added to a solution of 300 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (example 1, step 2) in 8 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 48 hours. After the addition of 50 ml of water and extraction with ethyl acetate, the organic phases are combined and then dried over magnesium sulfate, filtered through sintered glass, and concentrated under reduced pressure. After purification of the residue by silica column chromatography, elution being carried out with a mixture of dichloromethane and 7N ammoniacal methanol (90/10), 180 mg of 6-(morpholin-4-yl)-2-{2-[4-(morpholin-4-yl)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}pyrimidin-4(3H)-one are obtained in the form of a purple powder, the characteristics of which are the following:

후처리

  1. dry with materialdried over magnesium sulfate
  2. filtrationfiltered through sintered glass
  3. concentrationconcentrated under reduced pressure
  4. customAfter purification of the residue
  5. washby silica column chromatography, elution
  6. additionbeing carried out with a mixture of dichloromethane and 7N ammoniacal methanol (90/10), 180 mg of 6-(morpholin-4-yl)-2-{2-[4-(morpholin-4-yl)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}pyrimidin-4(3H)-one
  7. customare obtained in the form of a purple powder

출처 및 근거

ORD 기록
ord-727627765efb4782b1911c3b89f2f840
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133168B2

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