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

HRID 1711107Notes

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 175 (500 mg, 2 mmol) and methylamine hydrochloride (15 g, 222 mmol) in iso-propanol (50 ml) was heated at 130° C. in a sealed flask for four days. It was then cooled to room temperature, poured in water, and the pH was adjusted to 10 with 1N NaOH. After extraction of the aqueous phase with AcOEt, the combined organic phase was concentrated and purified by flash column chromatography (eluents 2% of NH4OH in methanol/CH2Cl2: 10/90 to 40/60) to afford title compound 421 (487 mg, 99% yield, hydrate form) as a beige solid. LCMS: 245.0 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-3c0994d6ee0c4ea486bbd5f8f9cb1ed4
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790729B2

Reaction notes

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