Dimethylformamide → HCID 178501266、化合物

HRID 1035715ノート

反応式

HRID 1035715 の反応式
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)=[O:4].C(N(C(C)C)CC)(C)C.[Cl:30][C:31]1[CH:32]=[C:33]([C:37]2[S:41][C:40]([NH2:42])=[N:39][N:38]=2)[CH:34]=[CH:35][CH:36]=1.CN(C=O)C>ClCCl.O>[Cl:30][C:31]1[CH:32]=[C:33]([C:37]2[S:41][C:40]([NH:42][C:16]([C:15]3[CH:14]=[CH:13][C:12]([O:11][C@@H:8]4[CH2:7][CH2:6][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9]4)=[CH:20][CH:19]=3)=[O:18])=[N:39][N:38]=2)[CH:34]=[CH:35][CH:36]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27723065-(3-Chlorophenyl)-1,3,4-thiadiazol-2-amineHCID 178501272HCID 178501272、化合物

生成物 1

HCID 178501266HCID 178501266、化合物収率 10.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

0.351 g of cis-4-(4-methoxycarbonylcyclohexyloxy)benzoic acid (1.26 mmol, 1 eq.) is placed in 5 mL of dichloromethane at room temperature. 0.42 mL of diisopropylethylamine (2.52 mmol, 2 eq.), 0.705 g of bromotris-pyrrolidinophosphonium hexafluorophosphonate (1.51 mmol, 1.2 eq.) and 0.267 g of 3-chlorophenyl-1,3,4-thiadiazol-2-amine (1.26 mmol, 1 eq.) are added successively. 2 mL of DMF are added. The reaction mixture is stirred for 1 day at room temperature, diluted in dichloromethane, and water is added. Filtration of this medium gives 0.06 g of methyl cis-4-{4-[5-(3-chlorophenyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenoxy}cyclohexanecarboxylate. The organic phase is separated out by settling, washed with water, dried over sodium sulfate, filtered and evaporated. The residue is taken up in ethanol, filtered off by suction and washed with diethyl ether. 0.090 g of methyl cis-4-{4-[5-(3-chlorophenyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenoxy}cyclohexanecarboxylate is obtained.

後処理

  1. filtrationFiltration of this medium

出典と根拠

ORDレコード
ord-b73a4786297b475b8eed74b75d126587
出典データセット
uspto-grants-2013_10
特許番号
US08546391B2

反応ノート

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