Sodium hydride → 2-(4-((3-(3-Chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexylidene)acetonitrile
Reaction equation
CCOP(OCC)([CH2:6][C:7]#[N:8])=O.CN1C(=O)N(C)CCC1.[H-].[Na+].[Cl:23][C:24]1[CH:25]=[C:26]([C:30]2[N:34]3[N:35]=[C:36]([NH:39][CH:40]4[CH2:45][CH2:44][C:43](=O)[CH2:42][CH2:41]4)[CH:37]=[CH:38][C:33]3=[N:32][CH:31]=2)[CH:27]=[CH:28][CH:29]=1>C1COCC1.O.CC(=O)OCC>[Cl:23][C:24]1[CH:25]=[C:26]([C:30]2[N:34]3[N:35]=[C:36]([NH:39][CH:40]4[CH2:45][CH2:44][C:43](=[CH:6][C:7]#[N:8])[CH2:42][CH2:41]4)[CH:37]=[CH:38][C:33]3=[N:32][CH:31]=2)[CH:27]=[CH:28][CH:29]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a 0° C. solution of diethyl cyanomethyl phosphonate (0.07 mL, 0.4 mmol) in THF (1.5 mL) was added DMPU (0.27 mL, 1 mmol), followed by NaH (15 mL, 0.37 mmol). After stirring for 10 min, a solution of 4-((3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexanone (130 mg, 0.38 mmol) in THF (1.5 mL) was added. The resulting mixture was stirred at room temperature for 2 h. TLC (EA) showed most of s.m. was converted into product. The mixture was poured into water (100 mL) and extracted with EtOAc (50 mL*3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo to give crude 2-(4-((3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexylidene)acetonitrile (100 mg, 69%) as a yellow solid.
Workup
- stirringThe resulting mixture was stirred at room temperature for 2 h
- extractionextracted with EtOAc (50 mL*3)
- dry with materialThe combined extracts were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-52b5c18ed2e9480c904f7677d65ae668
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09416132B2
Reaction notes
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