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Sodium Carbonate → 6-[4-Methoxybenzyl-(6-morpholinopyridin-3-yl)amino]-4-[(trifluoroacetyl)amino]pyridine-3-carboxylic acid ethyl ester

HRID 2035546
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HRID 2035546 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9](Cl)=[CH:10][C:11]=1[NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])=[O:5])[CH3:2].[CH3:20][O:21][C:22]1[CH:41]=[CH:40][C:25]([CH2:26][NH:27][C:28]2[CH:29]=[N:30][C:31]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:32][CH:33]=2)=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]([N:27]([CH2:26][C:25]2[CH:40]=[CH:41][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)[C:28]2[CH:29]=[N:30][C:31]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:32][CH:33]=2)=[CH:10][C:11]=1[NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])=[O:5])[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 634876Binap, (A+-)-HCID 674131333-(4-Methoxybenzyl)amino-6-morpholinopyridineHCID 866579426-Chloro-4-(trifluoroacetyl)aminopyridine-3-carboxylic acid ethyl ester

생성물 1

HCID 866579436-[4-Methoxybenzyl-(6-morpholinopyridin-3-yl)amino]-4-[(trifluoroacetyl)amino]pyridine-3-carboxylic acid ethyl ester

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

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온도
100 °C

실험 절차

21.8 mg of 6-chloro-4-(trifluoroacetyl)aminopyridine-3-carboxylic acid ethyl ester and 22 mg of 3-(4-methoxybenzyl)amino-6-morpholinopyridine were dissolved in 1 mL of toluene, to which 1.7 mg of palladium (II) acetate, 9.2 mg of 2,2′-bis (diphenylphosphino)-1,1′-binaphthyl and 202 mg of sodium carbonate were added, and stirred overnight at 100° C. After cooling, water was added to the reaction mixture, extracted with chloroform, the extract was washed with saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (hexane:ethyl acetate=1:1) to obtain 5.7 mg (ylod 14%) of the title compound as a light yellow solid.

후처리

  1. additionwere added
  2. temperatureAfter cooling
  3. extractionextracted with chloroform
  4. washthe extract was washed with saturated saline
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel thin layer chromatography (hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-451822e827f04f6d9cb107ac04030ad2
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08575153B2

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