Acetonitrile → Ethyl 2-(6-chloro-8-morpholinoimidazo[1,2-b]pyridazin-2-yl)acetate
Reaction equation
Br[C:2]1[C:3]2[N:4]([CH:9]=[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:11]=2)[N:5]=[C:6]([Cl:8])[CH:7]=1.C(#N)C.CCN(C(C)C)C(C)C.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>O>[Cl:8][C:6]1[CH:7]=[C:2]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[C:3]2[N:4]([CH:9]=[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:11]=2)[N:5]=1Participants
Procedure
Compound 28a (1.80 g, 5.66 mmol) was placed in a 20 mL vial equipped with a stir bar and then ACN (11 mL) was added. Once the mixture was homogeneous, DIEA (1.79 mL, 10.3 mmol) was added. Morpholine (0.601 mL, 6.90 mmol) was added and then the reaction was stirred at rt for 3 h during which time the entire solution solidified. The solid was broken up and additional ACN (2 mL) was added. The reaction was stirred for an additional 2 h at rt. The reaction was poured into water (50 mL) and the resulting precipitate was isolated by filtration. The solid was washed with water (2×20 mL) and then dried under reduced pressure to afford compound 28b. 1H-NMR (400 MHz, CDCl3) δ (ppm): 7.73 (s, 1H), 6.05 (s, 1H), 4.20 (q, J=7.1 Hz, 2H), 3.97-4.05 (m, 4H), 3.86-3.93 (m, 4H), 3.79 (s, 2H), 1.28 (t, J=7.2 Hz, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C14H17ClN4O3: 325.1 (M+H). Found: 325.1.
Workup
- customvial equipped with a stir bar
- stirringThe reaction was stirred for an additional 2 h at rt
- customthe resulting precipitate was isolated by filtration
- washThe solid was washed with water (2×20 mL)
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-d1718c31845f480dac7eb150c59ba80c
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193736B2
Reaction notes
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