Methanol → HCID 3027864, Verbindung

To a solution of amine 90 (300 mg, 0.62 mmol) and Goodman's reagent (392 mg, 1.00 mmol) in MeOH (60 mL) was added DIPEA (0.45 mL, 2.5 mmol) at room temperature. The reaction mixture was stirred for 7 h and then concentrated. The residue was dissolved in CHCl3 (200 mL) and washed with saturated NaHCO3 (2×100 mL). The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (silica gel, 90:9:1 CHCl3/CH3OH/NH4OH) to afford Boc-urea 92 (280 mg, 62%) as a light yellow solid: 1H NMR (300 MHz, CD3OD) δ 7.67 (t, J=7.8 Hz, 2H), 7.57 (s, 1H), 7.31 (d, J=8.1 Hz, 1H), 7.19 (s, 2H), 4.18 (t, J=5.4 Hz, 2H), 3.62 (t, J=6.0 Hz, 2H), 2.82 (t, J=6.3 Hz, 2H), 2.12 (t, J=5.7 Hz, 2H), 1.85-1.70 (m, 4H), 1.54 (s, 9H), 1.45 (s, 9H).

1. concentrationconcentrated
2. dissolutionThe residue was dissolved in CHCl3 (200 mL)
3. washwashed with saturated NaHCO3 (2×100 mL)
4. dry with materialThe organic layer was dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by column chromatography (silica gel, 90:9:1 CHCl3/CH3OH/NH4OH)

ORD-Eintrag

ord-45fdf47212cd4270b839b124fc9071d2

Quelldatensatz

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08124607B2