Propionic Acid → 2-(3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)azetidin-1-yl)quinoline

HRID 707345Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:14][CH:13]([NH:15][C:16]2[C:21]([NH2:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:12]1.[CH3:23][O:24][C:25](OC)(OC)OC.C(O)(=O)CC>>[CH3:23][O:24][C:25]1[N:15]([CH:13]2[CH2:14][N:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)[CH2:12]2)[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:21]2[N:22]=1

Participants

Reactant 3

HCID 1032Propionic Acid

HCID 74613Tetramethyl orthocarbonate

HCID 86694203N2-(1-(quinolin-2-yl)azetidin-3-yl)pyridine-2,3-diamine

Product 1

HCID 866942042-(3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)azetidin-1-yl)quinolineYield 59%

Conditions

Temperature: 90 °C

Procedure

N2-(1-Quinolin-2-yl-azetidin-3-yl)-pyridine-2,3-diamine (150 mg, 0.51 mmol) was combined with tetramethylorthocarbonate (1 mL) and propionic acid (8 mg) and heated at 90° C. for 2 hours. After that, the reaction solution was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel to give 2-(3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)azetidin-1-yl)quinoline (100 mg, 0.30 mmol, 59% yield). M+1: 332. 1H NMR (CDCl3, 400 MHz): δ(ppm) 8.06-8.05 (m, 1 H); 7.87-7.85 (m, 1 H); 7.72-7.68 (m, 2 H); 7.58-7.47 (m, 2 H); 7.20-7.17 (m, 1 H); 7.06-7.03 (m, 1 H); 6.62-6.60 (m, 1 H); 5.62-5.55 (m, 1 H); 4.84-4.80 (m, 2 H); 4.61-4.57 (m, 2 H); 4.10 (s, 3 H).

Workup

concentrationAfter that, the reaction solution was concentrated under reduced pressure
customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-9e3b9560f47b4641867b9217893720cc
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174992B2

Reaction notes

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