Methylamine → HCID 59189752, compound

Temperature

60 °C

A solution of 40% methylamine in methanol (49 μL, 0.48 mmol) was added to a solution of 2-aminocarbonylamino-6-(5-formylfuran-2-yl)indole-3-carboxamide (Compound 4-74, 0.10 g, 0.32 mmol) in anhydrous methanol (2 mL), and the mixture was stirred at 60° C. for 6 hours in a sealed tube. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in a solution mixture of methanol and tetrahydrofuran (methanol/tetrahydrofuran=1/2, 3 mL). Sodium borohydride (0.024 g, 0.64 mmol) was added to the solution mixture under ice-cooling, and the mixture was stirred at room temperature overnight. After the reaction mixture was concentrated under reduced pressure, the precipitated solid was washed with H2O (5 mL) and dried under reduced pressure to give the title compound (0.077 g) as a slightly brown solid (yield 74%).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionthe residue was dissolved in a solution mixture of methanol and tetrahydrofuran (methanol/tetrahydrofuran=1/2, 3 mL)
3. temperaturecooling
4. stirringthe mixture was stirred at room temperature overnight
5. concentrationAfter the reaction mixture was concentrated under reduced pressure
6. washthe precipitated solid was washed with H2O (5 mL)
7. customdried under reduced pressure

ORD record

ord-f3064ecf3af749059173a46f58a5a9f0

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08193237B2