Cesium carbonate → HCID 90051798、化合物

HRID 2284785

反応式

HRID 2284785 の反応式
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

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 27628302-Fluoropyridin-4-amineHCID 90052871HCID 90052871、化合物

生成物 1

HCID 90051798HCID 90051798、化合物

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-caa60730087b4e768c002328ec918c75
出典データセット
uspto-grants-2015_09
特許番号
US09145415B2

関連ノート

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