Hydrochloric Acid → HCID 11383098, compound

To a solution of the title compound provided by Example 12 (25 mg, 0.068 mmol) in tetrahydofuran (5 ml) and methanol (10 ml) was added sodium borohydride (20 mg, 0.53 mmol). After stirring for 1.5 hours, the mixture was treated with water (10 ml) and hydrochloric acid (1 M, 0.6 ml). The mixture was concentrated to a volume of 8 ml and the solid was collected by filtration. The solid was treated with aqueous sodium carbonate solution (10%, 10 ml) and extracted with ethyl acetate (3×30 ml). The combined extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography eluting with methanol-dichloromethane (5:95) to give the title compound (10 mg, 39% yield). 1H NMR (acetone-d6) δ1.36 (t, 3H, J=6.9 Hz, CH3), 3.95 (bs, 1H, OH), 4.09 (q, 2H, J=7.0 Hz, CH2), 4.56 (s, 2H, CH2), 5.28 (bs, 2H, NH2), 6.16 (d, 1H, J=1.1 Hz, Ar), 6.34 (d, 1H, J=1.1 Hz, Ar), 7.09 (d, 1H, J=8.5 Hz, Ar), 7.24 (d, 2H, J=8.8 Hz, Ar), 7.30–7.34 (m, 2H, Ar), 7.60–7.63 (m, 2H, Ar), 7.80 (s, 1H, NH).

1. concentrationThe mixture was concentrated to a volume of 8 ml
2. filtrationthe solid was collected by filtration
3. additionThe solid was treated with aqueous sodium carbonate solution (10%, 10 ml)
4. extractionextracted with ethyl acetate (3×30 ml)
5. dry with materialThe combined extracts were dried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by preparative thin layer chromatography
8. washeluting with methanol-dichloromethane (5:95)

ORD record

ord-1ab2fbf61c724f4fac2ff3c996f7ef5f

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07208507B2