Stannous Chloride → 1-(3-Methanesulfonyl-phenyl)-3-[2-(5,6,7,8-tetrahydro-isoquinolin-1-yl)-2H-pyrazol-3-yl]-1H-pyridazin-4-one
Reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:15]=2)[N:8]=1)=O.[C:25]1([NH:35]N)[C:34]2[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=2[CH:28]=[CH:27][N:26]=1.C1(N)C2CCCCC=2C=CN=1.N([O-])=O.[Na+].[Sn](Cl)Cl>>[CH3:23][S:20]([C:16]1[CH:15]=[C:14]([N:9]2[CH:10]=[CH:11][C:12](=[O:13])[C:7]([C:5]3[N:35]([C:25]4[C:34]5[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=5[CH:28]=[CH:27][N:26]=4)[N:2]=[CH:3][CH:4]=3)=[N:8]2)[CH:19]=[CH:18][CH:17]=1)(=[O:22])=[O:21]Participants
6
Reactant 5
Product 1
Procedure
Reaction of 3-((E)-3-dimethylamino-acryloyl)-1-(3-methansulfonyl-phenyl)-1H-pyridazin-4-one (A-7) and (5,6,7,8-tetrahydro-isoquinolin-1-yl)-hydrazine (prepared from the commercial 5,6,7,8-tetrahydro-isoquinolin-1-ylamine using sodium nitrite and tin(II) chloride in analogy to that described in J. Med. Chem. 2003, 46, 4676-4686) according to example 43 gave the desired product. MS: M=448.0 (M+H)+
Sources & evidence
- ORD record
- ord-9438331f3fe644618ce83c76aa321e2a
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178538B2
Reaction notes
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