Dimethylformamide → HCID 59189778, compound
Reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.[C:7]([BH3-])#N.[Na+].C([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]([C:30]#[N:31])[C:27]([NH2:29])=[O:28])(=O)C1C=CC=CC=1.C(=O)([O-])O.[Na+].C[N:38](C)[CH:39]=[O:40]>O.C(O)(=O)C>[NH2:38][C:39]([NH:31][C:30]1[NH:19][C:20]2[C:21]([C:26]=1[C:27]([NH2:29])=[O:28])=[CH:22][CH:23]=[C:24]([CH2:7][N:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1)[CH:25]=2)=[O:40]Participants
Procedure
Acetic acid (0.060 mL), thiomorpholine (0.12 mL, 1.2 mmol) and sodium cyanoborohydride (0.077 g, 1.2 mmol) were added to a solution of 2-aminocarbonylamino-6-formylindole-3-carboxamide (Compound 17-1, 0.10 g, 0.41 mmol) in anhydrous N,N-dimethylformamide (6 mL), and the mixture was stirred at room temperature overnight. Saturated sodium hydrogen carbonate aqueous solution (5 mL) and water (20 mL) were added to the reaction mixture, and the whole was extracted with ethyl acetate (30 mL). The organic layer was washed with brine (20 mL), and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resultant solid was washed with chloroform (2 mL), diethyl ether (2 mL), and dried under reduced pressure to give the title compound (0.062 g) as a colorless solid (yield 45%).
Workup
- extractionthe whole was extracted with ethyl acetate (30 mL)
- washThe organic layer was washed with brine (20 mL)
- dry with materialdried over anhydrous magnesium sulfate
- customAfter the solvent was evaporated under reduced pressure
- washthe resultant solid was washed with chloroform (2 mL), diethyl ether (2 mL)
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-25e2e5766b6a475a9ef3ffd30df94b6d
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193237B2
Reaction notes
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