Hydrochloric Acid → 1-[6-(2,5-Dimethylpyrrol-1-yl)pyridin-3-yl]-2-propylaminoethanol

HRID 2102355Notes

Reaction equation

[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[CH2:16][O:15]3)=[CH:10][N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[CH2:17]([NH2:20])[CH2:18][CH3:19].Cl.O>CS(C)=O>[CH3:1][C:2]1[N:3]([C:8]2[N:9]=[CH:10][C:11]([CH:14]([OH:15])[CH2:16][NH:20][CH2:17][CH2:18][CH3:19])=[CH:12][CH:13]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To the epoxide from example 40 (900 mg, 4.2 mmol) in DMSO (5 ml) was added propylamine (4 ml, 4.8 mmol) and the reaction mixture was heated to 40° C. for 4 days. The reaction mixture was then cooled and 3M HCl (aq) (10 ml) and water (10 ml) were added before washing with diethyl ether (2×10 ml). This organic layer was discarded. The aqueous layer was basified with NH4OH (5 ml) and extracted with ethyl acetate (3×10 ml). The organic extracts were combined and dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the title compound as an oil (1.15 g, 4.2 mmol, 100%). 1H NMR (CDCl3, 400 MHz) δ: 0.93 (t, 3H), 1.62 (m, 2H), 2.11 (s, 6H), 2.69-2.82 (m, 3H), 3.06 (dd, 1H), 3.60 (bs, 2H), 4.92 (dd, 1H), 5.84 (s, 2H), 7.20 (d, 1H), 7.88 (d, 1H), 8.61 (s, 1H). LRMS: m/z 274 (M-H+).

Workup

temperatureThe reaction mixture was then cooled
washbefore washing with diethyl ether (2×10 ml)
extractionextracted with ethyl acetate (3×10 ml)
dry with materialdried over anhydrous magnesium sulphate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-208138f4c2734dcaa003db1c41a731f4
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576081B2

Reaction notes

Loading…