Acetic Acid → 2-((3-(1-Carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylamino)methyl)-5-fluorobenzoic acid

A mixture of 4-(3-amino-2-methylphenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide (60.0 mg, 0.154 mmol), 5-fluoro-2-formylbenzoic acid (64.6 mg, 0.384 mmol), sodium triacetoxyborohydride (98 mg, 0.461 mmol), and acetic acid (0.022 mL, 0.384 mmol) in dichloroethane (3 mL) and tetrahydrofuran (2 mL) was stirred at room temperature for 16 hr and then quenched with water (3 mL). The resulting mixture was diluted with ethyl acetate (50 mL) and washed with water (25 mL). The aqueous solution was extracted with ethyl acetate (2×30 mL). The combined extract was washed with brine (25 mL) and dried over anhydrous MgSO4. The organic solution was concentrated under vacuum to dryness. The residue was dissolved with minimum amount of DMF, diluted with MeOH (3 mL), divided into 2 portions, and purified by reverse phase HPLC. The correct fractions were combined, concentrated under vacuum, and lyophilized to afford the desired product (TFA salt) (31.6 mg, 0.048 mmol, 31.3% yield) as a white powder.

1. customquenched with water (3 mL)
2. additionThe resulting mixture was diluted with ethyl acetate (50 mL)
3. washwashed with water (25 mL)
4. extractionThe aqueous solution was extracted with ethyl acetate (2×30 mL)
5. extractionThe combined extract
6. washwas washed with brine (25 mL)
7. dry with materialdried over anhydrous MgSO4
8. concentrationThe organic solution was concentrated under vacuum to dryness
9. dissolutionThe residue was dissolved with minimum amount of DMF
10. additiondiluted with MeOH (3 mL)
11. custompurified by reverse phase HPLC
12. concentrationconcentrated under vacuum

ORD record

ord-57f89fd601514956bc34b1b146d81754

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685969B2