Tolmetin → 1-(2-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]pyridin-5-yl}-3,3-dimethylurea

HRID 365619Notes

Reaction equation

HRID 365619 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][N:16]=3)=[CH:10][C:9]=2[CH3:22])=[O:7])=[CH:4][CH:3]=1.CC1C=C(CC(O)=O)N(C)C=1C(C1C=CC(Cl)=CC=1)=O.CC1C=CC(C(C2N(C)C(CC(O)=O)=CC=2)=O)=CC=1.[CH3:64][N:65]([CH3:69])[C:66](Cl)=[O:67]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:66]([N:65]([CH3:69])[CH3:64])=[O:67])=[CH:17][N:16]=3)=[CH:10][C:9]=2[CH3:22])=[O:7])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 5509TolmetinHCID 5733ZomepiracHCID 6598Dimethylcarbamoyl ChlorideHCID 15870202{2-[5-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]pyridin-5-yl}amine

Product 1

HCID 158702051-(2-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]pyridin-5-yl}-3,3-dimethylureaYield 57%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

{2-[5-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]pyridin-5-yl}amine [prepared by the method described in Example 5, but substituting the methyl ester of zomepirac for the methyl ester of tolmetin in Step (a)] (0.45 g, 1.32 mmol) and dimethylcarbamoyl chloride (0.13 ml, 1.46 mmol) were dissolved in pyridine (6.6 ml), and the mixture was stirred at room temperature for 96 h. The solvents were removed in vacuo and the residue was crystallized from chloroform-hexane mixture to give 1-{2-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]pyridin-5-yl}-3,3-dimethylurea (0.31 g, 57%) as a solid, mp 227.2-230.0° C.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was crystallized from chloroform-hexane mixture

Sources & evidence

ORD record
ord-0be4ca380c0344d0b801ae217aa53a08
Source dataset
uspto-grants-2000_10
Patent number
US06127402

Reaction notes

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