Cesium carbonate → HCID 90051798, 화합물

HRID 2284785

반응식

HRID 2284785 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([C:12]#[C:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][C@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:15]2)=[CH:4][N:3]=1.[NH2:28][C:29]1[CH:34]=[CH:33][N:32]=[C:31]([F:35])[CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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].O1CCOCC1>[F:35][C:31]1[CH:30]=[C:29]([NH:28][C:2]2[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([C:12]#[C:13][C@@H:14]3[CH2:19][CH2:18][CH2:17][C@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:15]3)=[CH:4][N:3]=2)[CH:34]=[CH:33][N:32]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 27628302-Fluoropyridin-4-amineHCID 90052871HCID 90052871, 화합물

생성물 1

HCID 90051798HCID 90051798, 화합물

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

반응 조건

온도
150 °C

실험 절차

To tert-butyl ((1S,3R)-3-((2-chloro-4-(propylamino)pyrimidin-5-yl)ethynyl)cyclohexyl)carbamate (P1, 155 mg), 4-amino-2-fluoropyridine (89 mg), tris(dibenzylideneacetone)dipalladium(0) (36 mg), 4,5′-bis(diphenylphosphino)-9,9′-dimethylxanthene (45 mg) and cesium carbonate (381 mg), 1,4-dioxane (5 mL) was added at room temperature, the reaction vessel was sealed, and then the mixture was stirred at 150° C. for 1 hour by using a microwave reaction system. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 88 to 30% hexane in ethyl acetate) to obtain tert-butyl ((1S,3R)-3-((2-((2-fluoropyridin-4-yl)amino)-4-(propylamino)pyrimidin-5-yl)ethynyl)cyclohexyl)carbamate (P2).

후처리

  1. customthe reaction vessel was sealed
  2. customa microwave reaction system
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent, 88 to 30% hexane in ethyl acetate)

출처 및 근거

ORD 기록
ord-caa60730087b4e768c002328ec918c75
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145415B2

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