HRID36254

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7998

Propyl chloroformate

C4H7ClO2

结构：CCCCc1nn(-c2cc(N)ccc2Cl)c(=O)n1Cc1ccc(-c2ccccc2S(=O)(=O)NC(=O)c2ccccc2Cl)cc1

HCID10032193

未命名化合物

PRODUCTS

生成物

结构：CCCCc1nn(-c2cc(NC(=O)OCCC)ccc2Cl)c(=O)n1Cc1ccc(-c2ccccc2S(=O)(=O)NC(=O)c2ccccc2Cl)cc1

HCID10010207

未命名化合物

收率 65.7%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

溶剂HCID1049

Pyridine

C5H5N

PROCEDURE

实验过程

At room temperature, under N2, a solution of 20 mg (0.031 mmole) of 2-(5-amino-2-chlorophenyl)-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Example 60), 3.8 mg (0.031 mmole) of DMAP, 18.9 mg (0.154 mmole) of propyl chloroformate, and 1 mL pyridine was stirred overnight. After quenching with methanol and water, the organic material was extracted with EtOAc, washed with water and brine, and dried over sodium sulfate. The crude product obtained after filtration and removal of volatiles was flash chromatographed over silica gel (gradient elution with 0.5-5% MeOH/CH2Cl2) to give 15 mg (65%) of the desired compound as a white solid, mp >119° C. (gradual), homogeneous by TLC (9:1 MeOH/CH2Cl2), mass spectrum (FAB) m/e 736 (M+1)+.

WORKUP

后处理

customAfter quenching with methanol and water
extractionthe organic material was extracted with EtOAc
washwashed with water and brine
dry with materialdried over sodium sulfate
customThe crude product obtained
filtrationafter filtration and removal of volatiles
customchromatographed over silica gel (gradient elution with 0.5-5% MeOH/CH2Cl2)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-2ed56beeec4340a8b46c668a07cf5fec
来源数据集: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05411980
来源说明: uspto-grants-1995_05

反应 SMILES

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:44])=[C:6]([N:8]2[C:12](=[O:13])[N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[S:27](=[O:39])(=[O:38])[NH:28][C:29](=[O:37])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:36])=[CH:17][CH:16]=3)[C:10]([CH2:40][CH2:41][CH2:42][CH3:43])=[N:9]2)[CH:7]=1.Cl[C:46]([O:48][CH2:49][CH2:50][CH3:51])=[O:47]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH2:40]([C:10]1[N:11]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27](=[O:38])(=[O:39])[NH:28][C:29](=[O:37])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])=[CH:19][CH:20]=2)[C:12](=[O:13])[N:8]([C:6]2[CH:7]=[C:2]([NH:1][C:46]([O:48][CH2:49][CH2:50][CH3:51])=[O:47])[CH:3]=[CH:4][C:5]=2[Cl:44])[N:9]=1)[CH2:41][CH2:42][CH3:43]