3,5-Dichloroaniline → HCID 12213510、化合物

HRID 1062650ノート

反応式

HRID 1062650 の反応式
ClC1C(Cl)=NC2C(C=1)=CC=CC=2.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(C([O-])=O)#CC([O-])=O.ClC1C=C(C=C(Cl)C=1)N.[C:37]([C:43]([O:45][CH3:46])=[O:44])#[C:38][C:39]([O:41][CH3:42])=[O:40]>>[NH:13](/[C:38](=[CH:37]\[C:43]([O:45][CH3:46])=[O:44])/[C:39]([O:41][CH3:42])=[O:40])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

5

反応物 4

HCID 122813,5-DichloroanilineHCID 12980Dimethyl acetylenedicarboxylateHCID 109872152,3-dichloroquinolineHCID 131725207HCID 131725207、化合物

生成物 1

HCID 12213510HCID 12213510、化合物収率 80%

実験手順

The dichloroquinoline (represented by 4) may be synthesized as described by Heindel, N. D., et al., “CYCLIZATION OF ANILINE-ACETYLENE DICARBOXYLATE ADDUCTS: A MODIFIED CONRAD-LIMPACH METHOD FOR THE SYNTHESIS OF POTENTIAL ANTIMALARIALS,” J. Med. Chem. 11 1218–1221 (1968). 3,5-Dichloroaniline, (1) a dihaloaniline, is refluxed with dimethyl acetylenedicarboxylate to produce substituted diester (3) in approximately 80% yield. Upon heating in diphenyl ether, the fumarate ester under goes cyclization to the quinoline carboxylate (4). The ester (4) can be readily aminated to the tosylamine (5) as described by Harrison, B. L., et al., “4-[(CARBOXYMETHYL)OXYL]-AND 4-[(CARBOXYMETHYL)AMINO]-5,7-DICHLOROQUINOLINE-2-CARBOXYLIC ACID: NEW ANTAGONISTS OF THE STRYCHNINE-INSENSITIVE GLYCINE BINDING SITE ON THE N-METHYL-D-ASPARTATE RECEPTOR COMPLEX,” J. Med. Chem. 33 3130–3132 (1990). The tosylamine (5) was acylated with diphenylcarbamoyl chloride (6), followed by hydrolysis, to form the diphenyl urea derivative (7).

出典と根拠

ORDレコード
ord-979a98b74de0443c8c28fd8f8e97ae8b
出典データセット
uspto-grants-2005_11
特許番号
US06962930B1

反応ノート

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