(+-)-3-Quinuclidinol → HCID 11450046, compound

HRID 1441442Notes

Reaction equation

HRID 1441442 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.Cl[C:11]1[N:16]=[N:15][C:14]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)=[CH:13][CH:12]=1>>[NH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([C:14]2[N:15]=[N:16][C:11]([O:9][CH:3]3[CH:4]4[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]4)[CH2:2]3)=[CH:12][CH:13]=2)=[CH:18]1

Participants

3

Reactant 2

HCID 15381(+-)-3-QuinuclidinolHCID 27636113-(6-chloropyridazin-3-yl)-1H-indole

Product 1

HCID 11450046HCID 11450046, compound

Procedure

3-Quinuclidinol (Aldrich, 254 mg, 2 mmol) was coupled with 3-(6-chloropyridazin-3-yl)-1H-indole (Bionet, 458 mg, 2 mmol) at 60° C. for 16 hours according to the procedure of Example 7A. The title compound was purified by preparative HPLC (Xterra™, column, Xterra RP-18, 5 μm, 30×100 mm. Eluting Solvent, MeCN/H2O (NH4HCO3, 0.1 M, pH=10), (v. 90/10 to 10/90 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) as solid (400 mg, 63%). 1H NMR (MeOH-D4, 300 MHz) 1.50-1.64 (m, 1H), 1.71-1.93 (m, 2H), 2.00-2.15 (m, 1H), 2.29-2.36 (m, 1H), 2.78-3.04 (m, 5H), 3.43-3.55 (m, 1H), 5.24-5.32 (m, 1H), 7.12-7.25 (m, 3H), 7.42-7.48 (m, 1H), 7.87 (s, 1H), 8.01 (d, J=9.2 Hz, 1H), 8.26-8.33 (m, 1H) ppm. MS (DCI/NH3) m/z 321 (M+H)+.

Workup

  1. customThe title compound was purified by preparative HPLC (Xterra™, column, Xterra RP-18, 5 μm, 30×100 mm. Eluting Solvent, MeCN/H2O (NH4HCO3, 0.1 M, pH=10), (v. 90/10 to 10/90 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) as solid (400 mg, 63%)

Sources & evidence

ORD record
ord-5105df03ebb94295a76b0b8a6174d2f3
Source dataset
uspto-grants-2010_02
Patent number
US07655657B2

Reaction notes

Loading…