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

HRID 584960Notes

Reaction equation

HRID 584960 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:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1>>[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:37](=[O:38])[C:36]4[CH:40]=[CH:41][C:33]([O:32][CH3:31])=[CH:34][CH:35]=4)[CH:12]=3)=[CH:22][CH:21]=2)[S:28]1

Participants

3

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 223414025-(3'-Methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione trifluoroacetate

Product 1

HCID 10183048N-[4'-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-4-methoxy-N-methylbenzamide

Procedure

In a manner similar to that of Example 37(e), by reacting 500 mg (1.1 mmol) of 5-(3′-methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione trifluoroacetate with 170 μl (1.25 mmol) of 4-methoxybenzoyl chloride, and after purification, 300 mg (50%) of N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-4-methoxy-N-methylbenzamide are obtained in the form of a white solid with a melting point of 170° C.

Workup

  1. customafter purification, 300 mg (50%) of N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-4-methoxy-N-methylbenzamide
  2. customare obtained in the form of a white solid with a melting point of 170° C.

Sources & evidence

ORD record
ord-85d3d9d2d4a34a0a92fc691126c4d0ea
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

Loading…