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Cesium carbonate → 5-((4-((3R)-3-cyano-3-ethyl-2-oxopyrrolidin-1-yl)pyrimidin-2-yl)amino)pyridine-2-carboxamide

HRID 714906
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HRID 714906 반응식
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][C@:10]([CH2:15][CH3:16])([C:13]#[N:14])[C:9]2=[O:17])[CH:5]=[CH:4][N:3]=1.[NH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([NH2:27])=[O:26])=[N:23][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:13]([C@@:10]1([CH2:15][CH3:16])[CH2:11][CH2:12][N:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([C:25]([NH2:27])=[O:26])=[N:23][CH:24]=3)[N:7]=2)[C:9]1=[O:17])#[N:14]
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참가 물질

7

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HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 104643925-Aminopyridine-2-carboxamideHCID 117840665(3R)-1-(2-chloropyrimidin-4-yl)-3-ethyl-2-oxopyrrolidine-3-carbonitrile

생성물 1

HCID 1178404975-((4-((3R)-3-cyano-3-ethyl-2-oxopyrrolidin-1-yl)pyrimidin-2-yl)amino)pyridine-2-carboxamide수율 8.9%

시약·촉매·용매

2
HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

To a solution of (3R)-1-(2-chloropyrimidin-4-yl)-3-ethyl-2-oxopyrrolidine-3-carbonitrile (200 mg) obtained in Step A of Example 8, 5-aminopyridine-2-carboxamide (130 mg) obtained in Step A of Example 350, cesium carbonate (520 mg) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (75 mg) in tetrahydrofuran (5.0 mL) was added tris(dibenzylideneacetone)dipalladium(0) (73 mg), and the mixture was stirred overnight at 80° C. under argon atmosphere. The insoluble substance was removed by filtration through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate), and recrystallized (diisopropyl ether/ethanol) to give the title compound (25 mg).

후처리

  1. customThe insoluble substance was removed by filtration through Celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)
  4. customrecrystallized (diisopropyl ether/ethanol)

출처 및 근거

ORD 기록
ord-205b1bc306954ff7ae5ee25b8fe6896d
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09187453B2

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