Triethylamine → HCID 15953425, compound

HRID 1696225Notes

Reaction equation

HRID 1696225 reaction equation
P(N=[N+]=[N-])([O:10][C:11]1C=CC=CC=1)(OC1C=CC=CC=1)=O.[CH3:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@@H:22]1[NH:27][C:28]1[C:33](C(O)=O)=[CH:32][N:31]=[C:30]2[NH:37][CH:38]=[CH:39][C:29]=12.C([N:42](CC)CC)C>C(O)(C)(C)C>[CH3:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@@H:22]1[N:27]1[C:28]2=[C:29]3[CH:39]=[CH:38][NH:37][C:30]3=[N:31][CH:32]=[C:33]2[NH:42][C:11]1=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 67277247HCID 67277247, compound

Product 1

HCID 15953425HCID 15953425, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

Diphenyl azidophosphate (0.083 mL) was added to 4-{[(1S,2R)-2-methylcyclohexyl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (56 mg) and triethylamine (0.075 mL) in tert-butanol (1.5 mL) and the mixture was stirred at 100° C. for 4 hours. tert-butanol was removed under reduced pressure, then chloroform and water were added, and the organic layer was separated, washed with brine, and dried over MgSO4. After removal of MgSO4 and solvent, the residue was purified by column chromatography on silica gel with chloroform and methanol (98:2 to 90:10) to give 1-[(1S,2R)-2-methylcyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (53 mg) as a white solid.

Workup

  1. customtert-butanol was removed under reduced pressure
  2. additionchloroform and water were added
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customAfter removal of MgSO4 and solvent
  7. customthe residue was purified by column chromatography on silica gel with chloroform and methanol (98:2 to 90:10)

Sources & evidence

ORD record
ord-c310459d9d224d7d8761ec561d915ee1
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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