Potassium Hydroxide → HCID 178483856, compound

To a solution of 18b (470 mg, 1.4 mmol) in 20 mL of anhydrous MeOH and 4 mL of anhydrous DMF under nitrogen was added hydroxylamine hydrochloride (258 mg, 3.7 mmol) and potassium hydroxide (206 mg, 3.7 mmol) and the resulting suspension was stirred at room temperature for 2 days. The reaction mixture was concentrated to dryness and the crude product was extracted with EtOAc (2×40 mL) and washed with brine solution (20 mL). The organic layer was dried over Na2SO4, filtered, washed with EtOAc and concentrated to dryness. The product was purified by column chromatography. The column was eluted with 4:1:0.5 chloroform:methanol:NH4OH and the desired fractions were combined, concentrated, and dried in vacuo to give a solid: yield 165 mg (32%), MS: m/z 367 (M+H)+; 1HNMR (DMSO-d6) δ 8.70 (bs, 1H, NOH), 8.33 (s, 1H, H-8), 8.15 (s, 1H, H-2), 7.27 (bs, 2H, 6-NH2), 5.86 (d, 1H, H-1′, J1′,2′=5.3 Hz), 5.43 (d, 1H, 2′-OH, J2′-2′=6.0 Hz), 5.35 (bs, 2H, C—NH2), 5.20 (d, 1H, 3′-OH, J3′-3′OH=5.2 Hz), 4.63 (ddd, 1H, H-2′, J1′,2′=5.3 Hz, J2′,3′=4.9 Hz, J2′-2′OH=6.0 Hz), 4.10 (ddd, 1H, H-3′, J2′,3′=4.9 Hz, J3′,4′=3.5 Hz, J3′-3′OH=5.2 Hz), 3.96-4.0 (m, 1H, H-4′), 2.64-2.75 (bm, 2H, 5′-CH2), 2.56 (t, 2H, N(CH3)—CH2), 2.20 (s, 3H, N—CH3), 2.09 (t, 2H, C—CH2). Anal. (C14H22N8O4.1.2C2H5OH.0.2CH3OH) C, H, N.

1. concentrationThe reaction mixture was concentrated to dryness
2. extractionthe crude product was extracted with EtOAc (2×40 mL)
3. washwashed with brine solution (20 mL)
4. dry with materialThe organic layer was dried over Na2SO4
5. filtrationfiltered
6. washwashed with EtOAc
7. concentrationconcentrated to dryness
8. customThe product was purified by column chromatography
9. washThe column was eluted with 4:1:0.5 chloroform
10. concentrationconcentrated
11. customdried in vacuo
12. customto give a solid

ORD record

ord-3828d5502529425cbbf4f741e9da3b38

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637485B2