Pyridine → HCID 178493029, compound

HRID 591944Notes

Reaction equation

Cl.[Cl:2][C:3]1[C:4]([N:26]2[CH2:31][C@@H:30]3[CH2:32][C@H:27]2[CH2:28][NH:29]3)=[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:14][C:13]=3[O:24][CH3:25])[NH:9][C:6]2=[N:7][CH:8]=1.[CH3:33][C@H:34]1[CH2:36][O:35]1.N1C=CC=CC=1.CCN(C(C)C)C(C)C>CO>[Cl:2][C:3]1[C:4]([N:26]2[CH2:31][C@@H:30]3[CH2:32][C@H:27]2[CH2:28][N:29]3[CH2:33][C@@H:34]([OH:35])[CH3:36])=[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:14][C:13]=3[O:24][CH3:25])[NH:9][C:6]2=[N:7][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

6-Chloro-7-(1S,4S)-2,5-diaza-bicyclo[2.2.1]hept-2-yl-2-(2-methoxy-4-morpholin-4-yl-phenyl)-3H-imidazo[4,5-b]pyridine hydrochloride (Compound XXXVII) (50 mg, 0.1 mmol), (S)-2-methyl-oxirane (7.30 mg, 0.126 mmol), pyridine (10.2 μL, 0.126 mmol), and methanol (3.0 mL) were stirred in a sealed tube at room temperature overnight. An additional equivalent each of epoxide and Hunig's base were added and the mixture was heated at 80° C. overnight. The mixture was concentrated and the material was subjected to purification via reverse phase chromatography (Gilson) to afford the title compound as a yellow lyophilate (26 mg, 50%). 1H NMR (d-chloroform): 13.63 (br s, 1H), 8.10 (m, 1H), 7.90 (s, 1H), 7.71 (s, 1H), 7.55 (s, 1H), 6.59 (m, 1H), 6.46 (s, 1H), 4.62 (m, 1H), 4.35 (m, 1H), 4.24 (t, J=7 Hz, 2H), 4.15 (s, 3H), 3.92 (s, 4H), 3.35 (s, 4H), 3.14 (m, 2H), 2.38 (m, 1H), 1.71 (m, 1H), 1.44 (m, 2H), 1.32 (m, 1H), 0.94 (m, 3H). MS: 499.18 (M+H). HPLC retention time: 1.83 minutes (G Method).

Workup

concentrationThe mixture was concentrated
customthe material was subjected to purification via reverse phase chromatography (Gilson)

Sources & evidence

ORD record: ord-ed412621562240bdb4366094fcf45d4b
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238656B2

Reaction notes

Loading…