Dichloromethane → HCID 58382137, compound

HRID 1628021Notes

Reaction equation

HRID 1628021 reaction equation
[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

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 58382138HCID 58382138, compound

Product 1

HCID 58382137HCID 58382137, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-f5cc49f191d045c8854b4cd0612df8d7
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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