Water → HCID 67277269, compound

HRID 1696216Notes

Reaction equation

HRID 1696216 reaction equation
[CH:1]([Si:4]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[O:5][CH2:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][C@H:9]([NH:13][C:14]2[C:19](C(O)=O)=[CH:18][N:17]=[C:16]3[NH:23][CH:24]=[CH:25][C:15]=23)[CH2:8]1)([CH3:3])[CH3:2].C([N:34]([CH2:37]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:46])C=CC=CC=1.O>O1CCOCC1>[CH:26]([Si:4]([CH:29]([CH3:31])[CH3:30])([CH:1]([CH3:3])[CH3:2])[O:5][CH2:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][C@H:9]([N:13]2[C:14]3=[C:15]4[CH:25]=[CH:24][NH:23][C:16]4=[N:17][CH:18]=[C:19]3[NH:34][C:37]2=[O:46])[CH2:8]1)([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 67277779HCID 67277779, compound

Product 1

HCID 67277269HCID 67277269, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-{[cis-3-{[(triisopropylsilyl)oxy]methyl}-cyclohexyl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (1.06 g) in dioxane (28 ml) was added triethylamine (1.33 ml) and diphenylphosphoryl azide (2.86 ml). After stirring at 120° C. for 4 hours, the reaction mixture was poured into water, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography on silica gel with n-hexane:EtOAc=60:40-35:65 to give 1-[cis-3-{[(triisopropylsilyl)oxy]methyl}cyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (970 mg) as a yellow powder.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel with n-hexane

Sources & evidence

ORD record
ord-39172009d2394a489db47a4079fadc99
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

Loading…