Acetonitrile → 2-Aminomethyl-5-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-phenol

To a solution of (1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (0.375 g, 0.99 mmol) in CH3CN (5 mL) was added N,N-diisopropylethylamine (0.35 mL, 2.00 mmol) followed by a solution of (5-bromomethyl-2-cyano-phenyl)acetate (0.318 g, 1.25 mmol) in CH3CN (5 mL). The resultant mixture was heated to 60° C. for 15 hours then cooled to room temperature. The mixture was concentrated and the residue was partitioned between CH2Cl2 (40 mL) and brine (10 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by column chromatography on silica gel (20:1 CH2Cl2—CH3OH) followed by radial chromatography on silica gel (2 mm plate, 2:1 hexanes-EtOAc) provided 0.28 g (51%) of a tan foam.

1. concentrationThe mixture was concentrated
2. customthe residue was partitioned between CH2Cl2 (40 mL) and brine (10 mL)
3. customThe phases were separated
4. extractionthe aqueous phase was extracted with CH2Cl2 (3×10 mL)
5. dry with materialThe combined organic extracts were dried (Na2SO4)
6. concentrationconcentrated
7. customPurification of the crude material by column chromatography on silica gel (20:1 CH2Cl2—CH3OH)

ORD-Eintrag

ord-65d5a238821740ba9d79175eeb4252c5

Quelldatensatz

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07807694B2