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Pyrazine → 8-cyclohexyl-3-tosyl-3H-dipyrrolo[1,2-a:2',3'-e]pyrazine

HRID 2204549
ノート
印刷プレビュー

反応式

HRID 2204549 の反応式
[CH:1]1([C:7](=O)[CH2:8][CH2:9][C:10]2[N:11]=[C:12]3[CH:18]=[CH:17][N:16]([S:19]([C:22]4[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[C:13]3=[N:14][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O(C1C=CC(P2(=S)SP(=S)(C3C=CC(OC4C=CC=CC=4)=CC=3)S2)=CC=1)C1C=CC=CC=1.N1C=CN=CC=1>C1COCC1.CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH:1]1([C:7]2[N:11]3[C:12]4[CH:18]=[CH:17][N:16]([S:19]([C:22]5[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=5)(=[O:21])=[O:20])[C:13]=4[N:14]=[CH:15][C:10]3=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 9261PyrazineHCID 118134142,4-Bis(4-phenoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetaneHCID 580100201-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)propan-1-one

生成物 1

HCID 580099938-cyclohexyl-3-tosyl-3H-dipyrrolo[1,2-a:2',3'-e]pyrazine

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒
HCID 8857
Ethyl Acetate
溶媒
HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of 1-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)propan-1-one (0.050 g, 0.12 mmol) in THF (2 mL) was added 2,4-bis(4-phenoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (0.071 g, 0.13 mmol, TCI). After about 6 h at ambient temperature, the reaction mixture was diluted with EtOAc (50 mL) and NaHCO3 (50 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel eluting with a gradient of 40-90% EtOAc in heptanes to provide 8-cyclohexyl-3-tosyl-3H-dipyrrolo[1,2-a:2;3′-e]pyrazine as a tan solid (0.020 g, 42%). LC/MS (Table 2, Method a) Rt=3.39 min; MS m/z: 394 (M+H)+.

後処理

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by chromatography on silica gel eluting with a gradient of 40-90% EtOAc in heptanes
  6. customto provide 8-cyclohexyl-3-tosyl-3H-dipyrrolo[1,2-a

出典と根拠

ORDレコード
ord-eed698d8b39347a493c265177929cd4b
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09365579B2

反応ノート

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