Diisopropylethylamine → N-(4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-2[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amino]-benzamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733207	—
Reactant	7-Amino-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one	HCID 14476478	—
Reactant	2-[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amino]-benzoic acid	HCID 66415425	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	N-(4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-2[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amino]-benzamide	HCID 10071896	—

Reaction Steps

A mixture of 2-[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amino]-benzoic acid (Step A, Example 113) (200 mg), 7-amino-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (143 mg), TBTU (265 mg), and DIEA (0.14 mL) in DMF (2 mL) was stirred at RT under N2 atmosphere for 16 h. The mixture was diluted with EtOAc (10 mL) and extracted with water (2×15 mL). The organic layer was dried over Na2SO4 and the crude material was purified by flash chromatography (SiO2, 5% MeOH/CH2Cl2) to afford the titled compound as a white solid. MS (ES+): 440.0 (M+H)+. Calc'd for C26H25N5O2-439.52.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07307088B2
Source dataset	uspto-grants-2007_12
ORD ID	ord-2151affb0ee44aa2a655bbad3c311d1a
Source note	uspto-grants-2007_12