HRID1185532

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID81531

Diisopropylethylamine

C8H19N

HCID516892

Sodium Bicarbonate

CHNaO3

结构：CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F

HCID9886157

Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

C10H15F6N6OP

HCID68598169

未命名化合物

结构：Cc1ccc2c(OCC(=O)N3CCC[C@H]3C(=O)NC3CCC3)cc(C(=O)O)nc2c1

HCID68599277

未命名化合物

PRODUCTS

生成物

结构：CCCCOC(=O)N1CCN(C(=O)[C@H](CF)NC(=O)c2cc(OCC(=O)N3CCC[C@H]3C(=O)NC3CCC3)c3ccc(C)cc3n2)CC1

HCID68602093

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

To a solution of 108 mg 4-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid in 2.5 ml DMF were added 134 μl DIPEA and 97 mg HATU. After 5 minutes 102 mg 4-((R)-2-Amino-3-fluoro-propionyl)piperazine-1-carboxylic acid butyl ester hydrotrifluoroacetate were added and the mixture stirred for 3 h before 2 ml of saturated aqueous NaHCO3 were added. The mixture was loaded on a chem Elute® cartridge and the crude product eluted with DCM. Further purification was performed by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA). The fractions containing the product were lyophilized to yield the pure product. Yield: 76 mg MS(ES+): m/e=669.

WORKUP

后处理

additionwere added
washElute® cartridge
washthe crude product eluted with DCM
customFurther purification
washC18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA)
additionThe fractions containing the product
customto yield the pure product

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-fd67a21426e9477187e698a2bbd2a6e5
来源数据集: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08669266B2
来源说明: uspto-grants-2014_03

反应 SMILES

[CH:1]1([NH:5][C:6]([C@@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13](=[O:30])[CH2:14][O:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([CH3:26])=[CH:23][CH:24]=3)[N:19]=[C:18]([C:27](O)=[O:28])[CH:17]=2)=[O:7])[CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:64]([O:68][C:69]([N:71]1[CH2:76][CH2:75][N:74]([C:77](=[O:82])[C@@H:78]([NH2:81])[CH2:79][F:80])[CH2:73][CH2:72]1)=[O:70])[CH2:65][CH2:66][CH3:67].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:64]([O:68][C:69]([N:71]1[CH2:72][CH2:73][N:74]([C:77](=[O:82])[C@@H:78]([NH:81][C:27]([C:18]2[CH:17]=[C:16]([O:15][CH2:14][C:13]([N:9]3[CH2:10][CH2:11][CH2:12][C@H:8]3[C:6](=[O:7])[NH:5][CH:1]3[CH2:2][CH2:3][CH2:4]3)=[O:30])[C:25]3[C:20](=[CH:21][C:22]([CH3:26])=[CH:23][CH:24]=3)[N:19]=2)=[O:28])[CH2:79][F:80])[CH2:75][CH2:76]1)=[O:70])[CH2:65][CH2:66][CH3:67]