Triethylamine → HCID 67278437, compound

HRID 1696213Notes

Reaction equation

HRID 1696213 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9]1[C:14](C(O)=O)=[CH:13][N:12]=[C:11]2[N:18]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:20][C:10]=12.C([N:31]([CH2:34]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:43])C=CC=CC=1.CCOC(C)=O>O1CCOCC1.O>[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[C:9]2=[C:10]3[CH:20]=[CH:19][N:18]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:11]3=[N:12][CH:13]=[C:14]2[NH:31][C:34]1=[O:43]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 67278153HCID 67278153, compound

Product 1

HCID 67278437HCID 67278437, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-{[(1S,2R)-2-methylcyclohexyl]amino}-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (3.9 g) and triethylamine (5.11 mL) in dioxane (39 mL) was added diphenylphosphoryl azide (5.0 mL) and the mixture was stirred at 120° C. for 3 hours. To the mixture were added EtOAc and water. The organic layer was separated and extracted with EtOAc. The extract was washed with saturated aqueous sodium hydrogencarbonate and brine, dried over MgSO4, filtrated and evaporated. The residue was purified by column chromatography on silica gel with EtOAc and n-hexane (1:4 to 1:2) to give 1-[(1S,2R)-2-methylcyclohexyl]-6-{[2-(trimethylsilyl)ethoxy]methyl}-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (3.33 g) as a white powder.

Workup

  1. customThe organic layer was separated
  2. extractionextracted with EtOAc
  3. washThe extract was washed with saturated aqueous sodium hydrogencarbonate and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltrated
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel with EtOAc and n-hexane (1:4 to 1:2)

Sources & evidence

ORD record
ord-78374331d496466c94056e15c9fa0c99
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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