HCID 86611710, compound → HCID 178466727, compound
Reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[CH:10]=[C:11]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][CH:21]=3)[C:12]3[N:13]([C:15](Cl)=[CH:16][N:17]=3)[N:14]=2)[CH2:4][CH2:3]1.NC1CCC(NC2C=C(NC3C=CC(OCC)=CC=3)C3N(C(Cl)=C(Cl)N=3)N=2)CC1>>[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH3:28])=[CH:24][CH:25]=3)[C:12]3[N:13]([CH:15]=[CH:16][N:17]=3)[N:14]=2)[CH2:4][CH2:3]1Participants
Procedure
To a mixture of crude N6-(4-aminocyclohexyl)-2,3,7-trichloro-N8-(4-ethoxyphenyl)imidazo[1,2-b]pyridazine-6,8-diamine from if as a free base (140 mg, 0.300 mmol) in EtOH (10 ml) in a 500 ml PARR bottle was added 10% Palladium on carbon (175 mg). The PARR bottle was then charged with H2 at 55 psi and allow to shake at room temperature for 24 hours. The catalyst was then filtered and the filtrate was concentrated in vacuo to give a crude mixture of 3 compounds. This mixture was purified by preparative HPLC to give 4.7 mg of Example I(1), N6-(4-aminocyclohexyl)-N8-(4-ethoxyphenyl)imidazo[1,2-b]pyridazine-6,8-diamine as a TFA salt, LC/MS, m/e 367 (M+1). 9.0 mg of N6-(4-aminocyclohexyl)-3-chloro-N8-(4-ethoxyphenyl)imidazo[1,2-b]pyridazine-6,8-diamine, LC/MS, m/e 401 (M+1) and 18.5 mg of N6-(4-aminocyclohexyl)-2,3-dichloro-N8-(4-ethoxyphenyl)imidazo[1,2-b]pyridazine-6,8-diamine, LC/MS, m/e 435 (M+1).
Sources & evidence
- ORD record
- ord-e69d199cf3d2408e92b60e29892beff3
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723336B2
Reaction notes
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