2-Thiophenecarbonyl chloride → N-[4'-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylthiophene-2-carboxamide

HRID 584970Notes

Reaction equation

HRID 584970 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.[S:31]1[CH:35]=[CH:34][CH:33]=[C:32]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]([C:32]4[S:31][CH:35]=[CH:34][CH:33]=4)=[O:37])[CH:12]=3)=[CH:22][CH:21]=2)[S:28]1

Participants

3

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 223414025-(3'-Methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione trifluoroacetate

Product 1

HCID 10203406N-[4'-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylthiophene-2-carboxamide

Procedure

In a manner similar to that of Example 37(e), by reacting 1 g (2.2 mmol) of 5-(3′-methylaminomethyl-biphenyl-4-ylmethyl)thiazolidine-2,4-dione trifluoro-acetate with 200 μl (2.5 mmol) of 2-thiophenecarboxylic acid chloride, and after purification, 500 mg (50%) of N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylthiophene-2-carboxamide are obtained in the form of a white solid with a melting point of 160° C.

Workup

  1. customafter purification, 500 mg (50%) of N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylthiophene-2-carboxamide
  2. customare obtained in the form of a white solid with a melting point of 160° C.

Sources & evidence

ORD record
ord-89e5b395d8cd42cb81206f01ff67dbb3
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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