HRID546537

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11198

Ethylamine hydrochloride

C2H8ClN

HCID2723939

1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

C8H18ClN3

HCID2796029

1H-Benzotriazol-1-ol--water (1/1)

C6H7N3O2

反应SMILES：CN1CCc2nc(C(=O)N[C@@H]3C[C@@H](C(=O)O)CC[C@@H]3NC(=O)c3cc4cc(Cl)ccc4[nH]3)sc2C1

HCID44593556

未命名化合物

PRODUCTS

产物

反应SMILES：CCNC(=O)[C@H]1CC[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)[C@H](NC(=O)c2nc3c(s2)CN(C)CC3)C1.Cl

HCID67056576

未命名化合物

收率 87.9%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

Dimethylformamide

C3H7NO

溶剂HCID8471

Triethylamine

C6H15N

PROCEDURE

实验过程

(1S,2R,4S)-4-Carboxy-N1-[(5-chloroindol-2-yl)carbonyl]-N2-[(5-methyl-4,5,6,7-tetrahydrothiazolo-[5,4-c]pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine (150 mg) was dissolved in N,N-dimethylformamide (3 ml), to which N-ethylamine hydrochloride (119 mg), 1-hydroxybenzotriazole monohydrate (79 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (112 mg) and triethylamine (326 μl) were added, and the mixture was stirred at room temperature for 4 days. The solvent was distilled off under reduced pressure, and a saturated aqueous solution of sodium hydrogencarbonate was added to the residue to conduct extraction with dichloromethane. The resultant organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by flash column chromatography on silica gel (dichloromethane:methanol=47:3). The thus-obtained white solid was dissolved in dichloromethane, to which 1N ethanol solution (171 μl) of hydrochloric acid was added. The solvent was distilled off under reduced pressure, and methanol and diethyl ether were added to the residue to collect precipitate formed by filtration, thereby obtaining the title compound (74 mg) as white solid.

WORKUP

后处理

additionwere added
distillationThe solvent was distilled off under reduced pressure
additiona saturated aqueous solution of sodium hydrogencarbonate was added to the residue
extractionextraction with dichloromethane
dry with materialThe resultant organic layer was dried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resultant residue was purified by flash column chromatography on silica gel (dichloromethane:methanol=47:3)
dissolutionThe thus-obtained white solid was dissolved in dichloromethane, to which 1N ethanol solution (171 μl) of hydrochloric acid
additionwas added
distillationThe solvent was distilled off under reduced pressure, and methanol and diethyl ether
additionwere added to the residue
customto collect precipitate
customformed by filtration

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-b97107866f184755a5777e5f14c4d932
来源数据集: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US07935824B2
来源说明: uspto-grants-2011_05

反应SMILES

[C:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11]([C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([Cl:22])=[CH:17][CH:16]=3)=[O:12])[C@H:6]([NH:23][C:24]([C:26]2[S:27][C:28]3[CH2:29][N:30]([CH3:35])[CH2:31][CH2:32][C:33]=3[N:34]=2)=[O:25])[CH2:5]1)(O)=[O:2].Cl.[CH2:37]([NH2:39])[CH3:38].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(N(CC)CC)C>[ClH:22].[Cl:22][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:11]([NH:10][C@H:7]1[CH2:8][CH2:9][C@H:4]([C:1](=[O:2])[NH:39][CH2:37][CH3:38])[CH2:5][C@H:6]1[NH:23][C:24]([C:26]1[S:27][C:28]3[CH2:29][N:30]([CH3:35])[CH2:31][CH2:32][C:33]=3[N:34]=1)=[O:25])=[O:12])=[CH:21]2