Methanesulfonyl chloride → Methanesulfonic acid 3-[1-(4-chloro-3,5-diethoxy-benzyl)-piperidin-4-ylcarbamoyl]-5-methoxy-phenyl ester

HRID 502468Notes

Reaction equation

HRID 502468 reaction equation
[Cl:1][C:2]1[C:26]([O:27][CH2:28][CH3:29])=[CH:25][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:24])[C:15]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([OH:23])[CH:16]=3)[CH2:9][CH2:8]2)=[CH:4][C:3]=1[O:30][CH2:31][CH3:32].[CH3:33][S:34](Cl)(=[O:36])=[O:35].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[Cl:1][C:2]1[C:3]([O:30][CH2:31][CH3:32])=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([NH:13][C:14]([C:15]3[CH:16]=[C:17]([O:23][S:34]([CH3:33])(=[O:36])=[O:35])[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=3)=[O:24])[CH2:9][CH2:8]2)=[CH:25][C:26]=1[O:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68456085N-[1-(4-Chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-3-hydroxy-5-methoxy-benzamide

Product 1

HCID 86609561Methanesulfonic acid 3-[1-(4-chloro-3,5-diethoxy-benzyl)-piperidin-4-ylcarbamoyl]-5-methoxy-phenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to the procedure described in example 72a), N-[1-(4-chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-3-hydroxy-5-methoxy-benzamide (example 258) was reacted with methanesulfonyl chloride, N-ethyl-diisopropylamine in CH2Cl2 at rt to yield the title compound as colorless solid. MS: 541.2 (MH+).

Sources & evidence

ORD record
ord-95cd35329bed4b33adb265e297c84cd0
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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