Water → 2-Aminocarbonylamino-6-azidomethylindole-3-carboxamide
Reaction equation
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2.[NH2:29][C:30]([NH:32][C:33]1[NH:34][C:35]2[C:40]([C:41]=1[C:42]([NH2:44])=[O:43])=[CH:39][CH:38]=[C:37]([CH2:45]O)[CH:36]=2)=[O:31].O>O1CCCC1>[NH2:29][C:30]([NH:32][C:33]1[NH:34][C:35]2[C:40]([C:41]=1[C:42]([NH2:44])=[O:43])=[CH:39][CH:38]=[C:37]([CH2:45][N:15]=[N+:16]=[N-:17])[CH:36]=2)=[O:31]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Diphenylphosphoryl azide (42 μL, 0.19 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (29 μL, 0.19 mmol) were added to a solution of 2-aminocarbonylamino-6-hydroxymethylindole-3-carboxamide (Compound 16-1, 40 mg, 0.16 mmol) in anhydrous tetrahydrofuran (5 mL) under ice-cooling, the mixture was stirred at room temperature overnight. Water (10 mL) was added to the reaction mixture, and the whole was extracted with ethyl acetate (10 mL). The organic layer was washed with brine (20 mL) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (5.0 mg) as a yellow solid (yield 11%).
Workup
- temperaturecooling
- extractionthe whole was extracted with ethyl acetate (10 mL)
- washThe organic layer was washed with brine (20 mL)
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-44e89feb11b249e19d66e80b05704a5b
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193237B2
Reaction notes
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