4,5-dichloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine → 1-(5-(5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)-N-(4-methoxybenzyl)cyclobutanamine

HRID 2362715노트

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HRID 2362715 반응식
Cl[C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]2[N:9]([S:18]([C:21]3[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[C:10]([C:12]3[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=3)=[CH:11][C:3]=12.[CH3:28][O:29][C:30]1[CH:59]=[CH:58][C:33]([CH2:34][NH:35][C:36]2([C:40]3[S:41][C:42]([Sn](CCCC)(CCCC)CCCC)=[CH:43][N:44]=3)[CH2:39][CH2:38][CH2:37]2)=[CH:32][CH:31]=1>CN(C)C=O.C(OCC)(=O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:8][C:7]1[C:2]([C:42]2[S:41][C:40]([C:36]3([NH:35][CH2:34][C:33]4[CH:32]=[CH:31][C:30]([O:29][CH3:28])=[CH:59][CH:58]=4)[CH2:39][CH2:38][CH2:37]3)=[N:44][CH:43]=2)=[C:3]2[CH:11]=[C:10]([C:12]3[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=3)[N:9]([S:18]([C:21]3[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[C:4]2=[N:5][CH:6]=1

참가 물질

7

반응물 2

HCID 670029234,5-dichloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 67003559N-(4-methoxybenzyl)-1-(5-(tributylstannyl)thiazol-2-yl)cyclobutanamine

생성물 1

HCID 670035991-(5-(5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)-N-(4-methoxybenzyl)cyclobutanamine

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A solution of 4,5-dichloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (Example 113C) (1.3 g, 3.09 mmol) and N-(4-methoxybenzyl)-1-(5-(tributylstannyl)thiazol-2-yl)cyclobutanamine (Example 112C) (2.45 g, 4.35 mmol) in anhydrous N,N-dimethylformamide (10 mL) was degassed for about 15 minutes under nitrogen. Bis(triphenylphosphine)palladium(II) dichloride (0.108 g, 0.154 mmol) was added to the degassed solution, and reaction was put under nitrogen, sealed, and heated to 100° C. for 16 hours. The reaction was cooled and diluted with ethyl acetate and water. The layers were separated, and organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 40% to 50% ethyl acetate in hexanes, to provide the title compound. MS ESI(+) m/z 659.1 [M+H]+.

후처리

  1. customsealed
  2. temperatureThe reaction was cooled
  3. customThe layers were separated
  4. washorganic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluting with a gradient of 40% to 50% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-458ce8e2856b43ba93022f1ed43921cf
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691810B2

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