Dichloromethane → HCID 58382137、化合物

HRID 1628021ノート

反応式

HRID 1628021 の反応式
[CH:1]1([NH:7][C:8]2[C:13](C(O)=O)=[CH:12][N:11]=[C:10]3[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[CH:19][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P([N:42]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(Cl)Cl.[C:48]([O-:51])(O)=O.[Na+]>O1CCOCC1>[CH:1]1([N:7]2[C:8]3=[C:9]4[CH:19]=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:26])([CH3:25])[CH3:27])[C:10]4=[N:11][CH:12]=[C:13]3[NH:42][C:48]2=[O:51])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 58382138HCID 58382138、化合物

生成物 1

HCID 58382137HCID 58382137、化合物収率 70%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

4-(Cyclohexylamino)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (0.713 g, 1.83 mmol) and TEA (0.638 mL, 4.58 mmol) were combined in 1,4-dioxane (14 mL) to give a suspension. The mixture was stirred until the suspension had dissolved. Diphenylphosphoryl azide (0.790 mL, 3.66 mmol) was added and the reaction heated at about 100° C. for about 5 h. DCM (50 mL) and saturated aqueous NaHCO3 (25 mL) were added and the layers separated. The aqueous layer was extracted with DCM (25 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (40 g Silicycle™ column) eluting with 20-80% EtOAc in DCM. The solvents were removed under reduced pressure. The material was triturated with heptane and the solid was collected by vacuum filtration and washed with heptane. The solid was dried under vacuum at about 50° C. to a constant weight to give 1-cyclohexyl-6-((2-(trimethylsilyl)ethoxy)methyl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (0.501 g, 70%): LC/MS (Table 2, Method b) Rt=2.78 min.; MS m/z: 387 (M+H)+.

後処理

  1. customto give a suspension
  2. dissolutionhad dissolved
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with DCM (25 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography (40 g Silicycle™ column)
  10. washeluting with 20-80% EtOAc in DCM
  11. customThe solvents were removed under reduced pressure
  12. customThe material was triturated with heptane
  13. filtrationthe solid was collected by vacuum filtration
  14. washwashed with heptane
  15. customThe solid was dried under vacuum at about 50° C. to a constant weight

出典と根拠

ORDレコード
ord-f5cc49f191d045c8854b4cd0612df8d7
出典データセット
uspto-grants-2014_07
特許番号
US08785639B2

反応ノート

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