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

HRID 369401노트

반응식

HRID 369401 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

{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.

후처리

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

출처 및 근거

ORD 기록
ord-63535b907027468ab165123ec2278584
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06136844

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