Azatadine → Methyl-1-((4'-(N-(3-methoxyphenyl)-N-methylsulfamoyl)biphenyl-4-yl)methyl)azetidine-3-carboxylate
Reaction equation
C([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=3)[CH3:19])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=O.CN1CCC(=C2[C:43]3[N:44]=[CH:45]C=[CH:47][C:42]=3[CH2:41]CC3C=CC=CC2=3)CC1.FC1C=CC(N(CC2SC(C3C=CC([CH:71]=[O:72])=CC=3)=CC=2)C(C)C)=CC=1.Cl.N(CC(O)=[O:80])C>>[CH3:71][O:72][C:41]([CH:42]1[CH2:47][N:44]([CH2:45][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:10]=[CH:11][C:12]([S:15](=[O:17])(=[O:16])[N:18]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=4)[CH3:19])=[CH:13][CH:14]=3)=[CH:5][CH:4]=2)[CH2:43]1)=[O:80]Participants
5
Reactant 4
Product 1
Procedure
When the product of Step C and azatadine 3 methylcarboxylate hydrochloride were substituted for 4-(5-(((4-fluorophenyl)(isopropyl)amino)methyl)thiophen-2-yl)benzaldehyde and sarcosine hydrochloride, respectively, in Example 22, Step C, the similar process the title compound in 69% yield, as pale paste. 1H-NMR (CDCl3) 7.64 (d, 2H, J=8.8 Hz); 7.58 (d, 2H, J=8 Hz); 7.54 (d, 2H, J=8.15 Hz); 7.36 (d, 2H, J=8.12 Hz); 7.17 (t, 1H, J=8.14 Hz); 6.80 (dd, 1H, J=8.07, 2.21 Hz); 6.72 (t, 1H, J=2.10 Hz); 6.64 (dd, 1H, J=7.80, 1.67 Hz); 3.74 (s, 3H); 3.71 (s, 2H); 3.69 (s, 3H); 3.64-3.58 (m, 2H); 3.42-3.36 (m, 4H); 3.18 (s, 3H).
Sources & evidence
- ORD record
- ord-7d435c54d4f54fde83895cb066178989
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193716B2
Reaction notes
Loading…