3-(1-Methanesulphonylpiperidin-4-yl)-3-phenylpropionaldehyde → 2-(1-{3-[1-(Methylsulfonyl)piperidin-4-yl]-3-phenylpropyl}piperidin-4-yl)-1,3-thiazole-4-carboxylic acid
Reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH:11]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[S:21][CH:22]=[C:23]([C:25]([O:27]CC)=[O:26])[N:24]=3)[CH2:16][CH2:15]2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].CS(N1CCC(C(C2C=CC=CC=2)CC=O)CC1)(=O)=O.N1CCC(C2SC=C(C(OCC)=O)N=2)CC1>>[CH3:1][S:2]([N:5]1[CH2:6][CH2:7][CH:8]([CH:11]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([C:20]3[S:21][CH:22]=[C:23]([C:25]([OH:27])=[O:26])[N:24]=3)[CH2:18][CH2:19]2)[CH2:9][CH2:10]1)(=[O:4])=[O:3]Participants
4
Reactant 3
Product 1
Procedure
The ethyl 2-(1-{3-[1-(methylsulfonyl)piperidin-4-yl]-3-phenylpropyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate used as starting material was prepared by reductive amination of 3-[1-(methylsulfonyl)piperidin-4-yl]-3-phenylpropanal (prepared following Method I using 4-benzoyl-N-methanesulphonylpiperidine as starting material) with ethyl 2-piperidin-4-yl-1,3-thiazole-4-carboxylate (Method K) as the amine component.
Sources & evidence
- ORD record
- ord-15763013d78642f9bef42f96c2ee04ad
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07615555B2
Reaction notes
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