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Cesium carbonate → (3R,5S)-N-(2-[(2,3-Difluorobenzyl)thio]-6-methoxypyrimidin-4-yl)-3,5-dimethylpiperazine-1-sulfonamide

HRID 1025007
ノート
印刷プレビュー

反応式

HRID 1025007 の反応式
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([S:9]([NH2:12])(=[O:11])=[O:10])[CH2:3]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:54]1[CH:59]=[C:58]([O:60][CH3:61])[N:57]=[C:56]([S:62][CH2:63][C:64]2[CH:69]=[CH:68][CH:67]=[C:66]([F:70])[C:65]=2[F:71])[N:55]=1.[Cl-].[NH4+]>O1CCOCC1.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].O.CCOC(C)=O>[F:71][C:65]1[C:66]([F:70])=[CH:67][CH:68]=[CH:69][C:64]=1[CH2:63][S:62][C:56]1[N:55]=[C:54]([NH:12][S:9]([N:4]2[CH2:3][C@H:2]([CH3:1])[NH:7][C@H:6]([CH3:8])[CH2:5]2)(=[O:10])=[O:11])[CH:59]=[C:58]([O:60][CH3:61])[N:57]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 5

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 53628381(3R,5S)-3,5-dimethylpiperazine-1-sulfonamideHCID 866198774-Chloro-2-([(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine2 回

生成物 1

HCID 59558797
(3R,5S)-N-(2-[(2,3-Difluorobenzyl)thio]-6-methoxypyrimidin-4-yl)-3,5-dimethylpiperazine-1-sulfonamide

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of (3R,5S)-3,5-dimethylpiperazine-1-sulfonamide (the product of example 72, 0.26 g), tris(dibenzylideneacetone)-dipalladium (0) (61 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (XPHOS) (32 mg), cesium carbonate (0.32 g) and 4-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine (the product of example 35 step i, 0.20 g) in anhydrous dioxane (8 ml) was heated at reflux in a microwave at 100° C., 300 W, open vessel with cooling for 15 min. Saturated aqueous ammonium chloride (5 ml) and EtOAc (Snail) were added, followed by H2O. The layers were separated and the organic layer extracted with H2O (×3). The organic layer was discarded and the combined aqueous extracts exhaustively extracted with further EtOAc. These extracts were combined, washed with saturated aqueous sodium chloride, dried with sodium sulfate, filtered and evaporated. The resulting solid was washed with H2O to afford the title compound as a white solid. Yield: 0.111 g

後処理

  1. temperaturewas heated
  2. temperature300 W, open vessel with cooling for 15 min
  3. customThe layers were separated
  4. extractionthe organic layer extracted with H2O (×3)
  5. extractionthe combined aqueous extracts exhaustively extracted with further EtOAc
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. washThe resulting solid was washed with H2O

出典と根拠

ORDレコード
ord-a5d55ae530d843efb1cbf27eb03c677d
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722883B2

反応ノート

読み込み中…

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