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

HRID 584971Notes

Reaction equation

HRID 584971 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1.[CH3:24][O:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29]>>[O:22]=[C:20]1[NH:19][C:18](=[O:23])[CH:17]([CH2:16][C:13]2[CH:12]=[CH:11][C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][N:2]([CH3:1])[C:28](=[O:29])[C:27]4[CH:31]=[CH:32][CH:33]=[CH:34][C:26]=4[O:25][CH3:24])[CH:5]=3)=[CH:15][CH:14]=2)[S:21]1

Participants

3

Reactant 2

HCID 889692-Methoxybenzoyl chlorideHCID 120854865-(3'-Methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione

Product 1

HCID 10276348N-[4'-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-2-methoxy-N-methylbenzamide

Procedure

In a manner similar to that of Example 37(e), by reacting 500 mg (1.5 mmol) of 5-(3′-methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione with 230 μl (1.5 mmol) of 2-methoxybenzoyl chloride, and after purification, 500 mg (70%) of N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-2-methoxy-N-methylbenzamide are obtained in the form of a white solid with a melting point of 96° C.

Workup

  1. customafter purification, 500 mg (70%) of N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-2-methoxy-N-methylbenzamide
  2. customare obtained in the form of a white solid with a melting point of 96° C.

Sources & evidence

ORD record
ord-a3ca62fce15e42bdb3ba7e0187dedd42
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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