Sodium Hydroxide → N-Methyl-2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-amine

HRID 2193772Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:12]=[CH:13][N:14]([CH3:16])[CH:15]=3)[S:10][C:3]=12.Cl.[CH3:18][NH2:19].[OH-].[Na+]>C(O)(C)C.O>[CH3:18][NH:19][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:12]=[CH:13][N:14]([CH3:16])[CH:15]=3)[S:10][C:3]=12

Participants

Conditions

Temperature: 130 °C

Procedure

A stirred suspension of 10 (500 mg, 2 mmol) and methylamine hydrochloride (15 g, 222 mmol) in isopropanol (50 ml) was heated at 130° C. in a sealed flask for four days, then cooled to room temperature. The reaction mixture was poured in water, and the pH was adjusted to ˜10 with 1N NaOH. After extraction of the aqueous phase with AcOEt, the combined organic layer was concentrated and directly purified by flash column chromatography (eluents 2% of NH4OH in methanol/CH2Cl2: 10/90 to 40/60) to afford title compound 344 (487 mg, 99% yield, hydrate form) as a beige solid. MS (m/z): 245.0 (M+H)+..

Workup

temperaturecooled to room temperature
extractionAfter extraction of the aqueous phase with AcOEt
concentrationthe combined organic layer was concentrated
customdirectly purified by flash column chromatography (eluents 2% of NH4OH in methanol/CH2Cl2: 10/90 to 40/60)

Sources & evidence

ORD record: ord-3bc86c328ce24d57988d904e7fb24ecb
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329726B2

Reaction notes

Loading…