2-[4-(N,N-Dimethylamino)-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-benzoylamino]-N-(5-chloropyridin-2-yl)benzamide → N-(5-chloropyridin-2-yl)-2-[4-(N,N-dimethylamino)-2-(piperidin-4-yloxy)benzoylamino]benzamide

HRID 644164Notes

Reaction equation

HRID 644164 reaction equation
[CH3:1][N:2]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([NH:10][C:11]2[CH:26]=[CH:25][CH:24]=[CH:23][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)=[O:14])=[O:9])=[C:6]([O:29][CH:30]2[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]2)[CH:5]=1)[CH3:3]>C(Cl)Cl.CCOCC>[CH3:3][N:2]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([NH:10][C:11]2[CH:26]=[CH:25][CH:24]=[CH:23][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)=[O:14])=[O:9])=[C:6]([O:29][CH:30]2[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]2)[CH:5]=1)[CH3:1]

Participants

3

Reactant 1

HCID 685339532-[4-(N,N-Dimethylamino)-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-benzoylamino]-N-(5-chloropyridin-2-yl)benzamide

Product 1

HCID 57860759N-(5-chloropyridin-2-yl)-2-[4-(N,N-dimethylamino)-2-(piperidin-4-yloxy)benzoylamino]benzamideYield 60%

Reagents, catalysts & solvents 1

HCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

Using a procedure similar to Example 1-G, 2-[4-(N,N-dimethylamino)-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide gave the desired product (638 mg, 60%) as a white solid after chromatography and CH2Cl2/ether trituration.

Sources & evidence

ORD record
ord-85daf07d1c694cdf85a1cacfa62a698c
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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