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

HRID 369401ノート

反応式

HRID 369401 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

{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.

後処理

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

出典と根拠

ORDレコード
ord-63535b907027468ab165123ec2278584
出典データセット
uspto-grants-2000_10
特許番号
US06136844

反応ノート

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