2-(Methylamino)ethanol → tert-butyl 4-((4-(N-(2-hydroxyethyl)-N-methylcarbamoyl)phenyl)bromomethylene)piperidine-1-carboxylate
Reaction equation
[OH:1][CH2:2][CH2:3][N:4](C)[C:5](=O)C1C=CC(C(C2C=CC=C3C=2N=CC=C3)=C2CCN(CC3N=CSC=3)CC2)=CC=1.CNCCO.[C:42]([O:46][C:47]([N:49]1[CH2:54][CH2:53][C:52](=[C:55]([Br:65])[C:56]2[CH:64]=[CH:63][C:59]([C:60](O)=[O:61])=[CH:58][CH:57]=2)[CH2:51][CH2:50]1)=[O:48])([CH3:45])([CH3:44])[CH3:43]>>[OH:1][CH2:2][CH2:3][N:4]([CH3:5])[C:60]([C:59]1[CH:63]=[CH:64][C:56]([C:55]([Br:65])=[C:52]2[CH2:51][CH2:50][N:49]([C:47]([O:46][C:42]([CH3:44])([CH3:43])[CH3:45])=[O:48])[CH2:54][CH2:53]2)=[CH:57][CH:58]=1)=[O:61]Participants
Procedure
A still further embodiment is directed to a process for preparing N-(2-hydroxyethyl)-N-methyl-4-(quinolin-8-yl(1-(thiazol-4-ylmethyl)piperidin-4-ylidene)methyl)benzamide comprising reacting 2-(methylamino)ethanol with 4-((1-(tert-butoxycarbonyl)piperidin-4-ylidene)bromomethyl)benzoic acid to form tert-butyl 4-((4-(N-(2-hydroxyethyl)-N-methylcarbamoyl)phenyl)bromomethylene)piperidine-1-carboxylate; reacting the tert-butyl 4-((4-(N-(2-hydroxyethyl)-N-methylcarbamoyl)phenyl)bromomethylene)piperidine-1-carboxylate with 8-quinolineboronic acid to form tert-butyl 4-((4-(N-(2-hydroxyethyl)-N-methylcarbamoyl)phenyl)(quinolin-8-yl)methylene)piperidine-1-carboxylate; deprotecting the tert-butyl 4-((4-(N-(2-hydroxyethyl)-N-methylcarbamoyl)phenyl)(quinolin-8-yl)methylene)piperidine-1-carboxylate to form N-(2-hydroxyethyl)-N-methyl-4-((piperidin-4-ylidene)(quinolin-8-yl)methyl)benzamide; and reacting the N-(2-hydroxyethyl)-N-methyl-4-((piperidin-4-ylidene)(quinolin-8-yl)methyl)benzamide with thiazole-4-carbaldehyde to form the N-(2-hydroxyethyl)-N-methyl-4-(quinolin-8-yl(1-(thiazol-4-ylmethyl)piperidin-4-ylidene)methyl)benzamide.
Sources & evidence
- ORD record
- ord-caeaac32674d4445b2486d298246e636
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977355B2
Reaction notes
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