N-(2-Aminoethyl)piperidine → n-{4-[4-Amino-7-((1e)-3-oxo-3-{[2-(1-piperidinyl)ethyl]amino}-1-propenyl)thieno[3,2-c]pyridin-3-yl]-2-methoxyphenyl}-1-methyl-1h-indole-2-carboxamide

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	N-(2-Aminoethyl)piperidine	HCID 33944	—
Edukt	Diisopropylethylamine	HCID 81531	—
Edukt	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Edukt	(2e)-3-[4-Amino-3-(3-methoxy-4-{[(1-methyl-1h-indol-2-yl)carbonyl]amino}phenyl)thieno[3,2-c]pyridin-7-yl]acrylic acid	HCID 18450569	—
Lösungsmittel	Dimethylformamide	HCID 6228	—
Lösungsmittel	1-Hydroxybenzotriazole	HCID 75771	—
Produkt	n-{4-[4-Amino-7-((1e)-3-oxo-3-{[2-(1-piperidinyl)ethyl]amino}-1-propenyl)thieno[3,2-c]pyridin-3-yl]-2-methoxyphenyl}-1-methyl-1h-indole-2-carboxamide	HCID 18451052	77,3%

Reaktionsschritte

A mixture of Example 271 (30.6 mg, 0.044 mmol), N,N-diisopropylethylamine (35 μL, 0.20 mmol), 2-piperidin-1-ylethylamine (14.3 μL, 0.10 mmol), and DMF (1 mL) was treated sequentially with 0.5M (0.09 mL) of HBTU in DMF and 0.5M (0.09 mL) of HOBT in DMF. The reaction was stirred for 24 hours at ambient temperature and partitioned between 1N NaOH and ethyl acetate. The combined extracts were dried (Na2SO4), filtered, and concentrated to provide the desired product (20.4 mg, 0.034 mmol). LCMS m/e 609.2; retention time: 2.93 min.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US07202363B2
Quelldatensatz	uspto-grants-2007_04
ORD ID	ord-5435f150aba64647ba79c01c5af57ea9
Quellennotiz	uspto-grants-2007_04