HRID2413199

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6228

N,N-Dimethylformamide

C3H7NO

2 次

HCID8471

Triethylamine

C6H15N

HCID10928

Ethyl chloroformate

C3H5ClO2

HCID20208677

未命名化合物

HCID178525356

未命名化合物

PRODUCTS

生成物

$结构：NC(=NCC(F)(F)F)Nc1ccnc(CCCCCNC(=O)CCc2c[nH]cn2)n1.NC(=NCC(F)(F)F)Nc1ccnc(CCCCCNC(=O)CCc2c[nH]cn2)n1.O.O=C(O)/C=C\C(=O)O.O=C(O)/C=C\C(=O)O.O=C(O)/C=C\C(=O)O.O=C(O)/C=C\C(=O)O$

HCID178512205

未命名化合物

PROCEDURE

实验过程

Ethyl chloroformate (0.14 ml.) was added to a stirred mixture of 3-(imidazol-4-yl)propionic acid (0.3 g.) and triethylamine (2 ml.) in DMF (5 ml.) at 0° and the mixture stirred at 0° for 0.5 hours. 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(5-aminopentyl)pyrimidine (0.3 g.) in DMF (2 ml.) was added to the mixture and stirring was continued at room temperature for 16 hours. The mixture was evaporated and the residue partitioned between EtOAc and 2 N aqueous HCl. The acid layer was basified with 11 N aqueous NaOH, extracted with EtOAc, dried (MgSO4) and evaporated to dryness. The residual gum was dissolved in EtOAc and treated with excess of a solution of maleic acid in EtOAc. The resulting solid was filtered and recrystallised from EtOH/EtOAc to give N-[5-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-yl)pentyl]-3-(imidazol-4-yl)propionamide bis maleate hemihydrate (containing 0.5 EtOH of crystallisation) (0.2 g.), m.p. 136°-141° (decomp.).

WORKUP

后处理

stirringstirring
waitwas continued at room temperature for 16 hours
customThe mixture was evaporated
customthe residue partitioned between EtOAc and 2 N aqueous HCl
extractionextracted with EtOAc
dry with materialdried (MgSO4)
customevaporated to dryness
dissolutionThe residual gum was dissolved in EtOAc
additiontreated with excess of a solution of maleic acid in EtOAc
filtrationThe resulting solid was filtered
customrecrystallised from EtOH/EtOAc

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-bd2c05f0aa0c4aa8b5265f01aa05792e
来源数据集: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04496571
来源说明: uspto-grants-1985_01

反应 SMILES

ClC([O:4][CH2:5][CH3:6])=[O:3].[NH:7]1[CH:11]=[C:10]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])[N:9]=[CH:8]1.C(N(CC)CC)C.[F:24][C:25]([F:44])([F:43])[CH2:26][N:27]=[C:28]([NH2:42])[NH:29][C:30]1[CH:35]=[CH:34][N:33]=[C:32]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][NH2:41])[N:31]=1.CN([CH:48]=[O:49])C>>[OH2:3].[C:5]([OH:4])(=[O:49])/[CH:6]=[CH:13]\[C:14]([OH:16])=[O:15].[C:48]([OH:49])(=[O:3])/[CH:12]=[CH:13]\[C:14]([OH:16])=[O:15].[F:44][C:25]([F:24])([F:43])[CH2:26][N:27]=[C:28]([NH2:42])[NH:29][C:30]1[CH:35]=[CH:34][N:33]=[C:32]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:14](=[O:16])[CH2:13][CH2:12][C:10]2[N:9]=[CH:8][NH:7][CH:11]=2)[N:31]=1.[F:44][C:25]([F:24])([F:43])[CH2:26][N:27]=[C:28]([NH2:42])[NH:29][C:30]1[CH:35]=[CH:34][N:33]=[C:32]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:14](=[O:16])[CH2:13][CH2:12][C:10]2[N:9]=[CH:8][NH:7][CH:11]=2)[N:31]=1.[C:5]([OH:4])(=[O:49])/[CH:6]=[CH:13]\[C:14]([OH:16])=[O:15].[C:5]([OH:4])(=[O:49])/[CH:6]=[CH:13]\[C:14]([OH:16])=[O:15]