Morpholine → Ethyl 6-chloro-8-morpholinoimidazo[1,2-b]pyridazine-2-carboxylate

HRID 718566Notes

Reaction equation

HRID 718566 reaction equation
Br[C:2]1[C:3]2[N:4]([CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:11]=2)[N:5]=[C:6]([Cl:8])[CH:7]=1.CCN(C(C)C)C(C)C.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C(#N)C>[Cl:8][C:6]1[CH:7]=[C:2]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:3]2[N:4]([CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:11]=2)[N:5]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 91756831Ethyl 8-bromo-6-chloroimidazo[1,2-b]pyridazine-2-carboxylate

Product 1

HCID 117728463Ethyl 6-chloro-8-morpholinoimidazo[1,2-b]pyridazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of compound 5a (10.6 g, 34.8 mmol) in acetonitrile (150 mL) was added DIEA (10.9 mL, 62.6 mmol) and morpholine (3.60 mL, 42.0 mmol). The reaction mixture was stirred at rt for 1 h, during which time the entire solution solidified. The resulting mixture was left at rt for 3 h, then was poured into ice water (200 mL), and the precipitates were collected by filtration, and dried under high vacuum. Compound 5b was obtained as a white solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.25 (s, 1H), 6.10 (s, 1H), 4.43 (q, J=7.1 Hz, 2H), 3.99-4.17 (m, 4H), 3.86-3.96 (m, 4H), 1.41 (t, J=7.1 Hz, 3H).

Workup

  1. waitThe resulting mixture was left at rt for 3 h
  2. filtrationthe precipitates were collected by filtration
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-e1fa0af8d5994de08e6b15bb597c7267
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

Loading…