m-Anisoyl chloride → N-[4'-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-3-methoxy-N-methylbenzamide

HRID 584961Notes

Reaction equation

HRID 584961 reaction equation
FC(F)(F)C(O)=O.[CH3:8][NH:9][CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][CH:41]=1)[C:36](Cl)=[O:37]>>[O:29]=[C:27]1[NH:26][C:25](=[O:30])[CH:24]([CH2:23][C:20]2[CH:19]=[CH:18][C:17]([C:13]3[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][N:9]([CH3:8])[C:36](=[O:37])[C:35]4[CH:39]=[CH:40][CH:41]=[C:33]([O:32][CH3:31])[CH:34]=4)[CH:12]=3)=[CH:22][CH:21]=2)[S:28]1

Participants

3

Reactant 2

HCID 74374m-Anisoyl chlorideHCID 223414025-(3'-Methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione trifluoroacetate

Product 1

HCID 10226492N-[4'-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-3-methoxy-N-methylbenzamide

Procedure

In a manner similar to that of Example 37(e), by reacting 540 mg (1.2 mmol) of 5-(3′-methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione trifluoroacetate with 300 μl (2 mmol) of 3-methoxybenzoyl chloride, and after purification, 400 mg (70%) of N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-3-methoxy-N-methylbenzamide are obtained in the form of a white solid with a melting point of 173° C.

Workup

  1. customafter purification, 400 mg (70%) of N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-3-methoxy-N-methylbenzamide
  2. customare obtained in the form of a white solid with a melting point of 173° C.

Sources & evidence

ORD record
ord-525fe8a5468f4cdcb3ed9c365bf07e67
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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