Ethyl Acetate → HCID 68349556, compound
Reaction equation
[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:12]=[C:6]2[C:5]=1Cl)(=[O:3])[NH2:2].CC[N:21]([CH:25]([CH3:27])[CH3:26])C(C)C.[CH3:28][CH2:29]OC(C)=O.[CH3:34]N1C(=O)CCC1>>[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:12]=[C:6]2[C:5]=1[NH:21][C@@H:25]([C:26]1([CH3:34])[CH2:29][CH2:28]1)[CH3:27])(=[O:3])[NH2:2]Participants
Procedure
A solution of ethyl 3-carbamoyl-4-chloropyrrolo[1,2-b]pyridazine-6-carboxylate (1.25 g, 4.67 mmol) (R)-1-(1-methylcyclopropyl)ethanamine (0.697 g, 5.14 mmol) and DIPEA (2.039 mL, 11.67 mmol) in NMP (Volume: 5 mL) was heated to 100° C. for 4 hr. The reaction mixture was added 100 mL of EtOAc which was washed with 50 mL of water, 50 mL of 10% LiCl solution and 50 mL of brine, dried over Na2SO4. Filtration and concentration to yield a crude product which was purified on silica gel column with hexanes/EtOAc(1/1) to yield the desired product (1.246 g, 81% yield). 1H NMR (400 MHz, CD3OD) δ 8.23 (s, 1H), 8.03 (d, J=1.8 Hz, 1H), 7.32 (d, J=1.8 Hz, 1H), 4.38 (d, J=7.0 Hz, 2H), 4.04-3.93 (m, 1H), 1.46-1.36 (m, 6H), 1.27 (s, 3H), 0.65-0.51 (m, 2H), 0.48-0.37 (m, 2H). MS (ES+) m/z: 331.08 (M+H); HPLC: 96%, retention time: 3.260 min (analytical HPLC Method B).
Workup
- washwas washed with 50 mL of water, 50 mL of 10% LiCl solution and 50 mL of brine
- dry with materialdried over Na2SO4
- filtrationFiltration and concentration
- customto yield a crude product which
- customwas purified on silica gel column with hexanes/EtOAc(1/1)
Sources & evidence
- ORD record
- ord-192d07553e6f4c5596a27fdd938c9515
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221826B2
Reaction notes
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