HRID1408017

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6228

N,N-Dimethylformamide

C3H7NO

HCID10367

2,6-Pyridinedicarboxylic acid

C7H5NO4

HCID81531

Diisopropylethylamine

C8H19N

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

结构：Nc1ccc(N2CCCCC2)cc1-c1cc(C(=O)NCc2cccc(C(F)(F)F)c2)ccn1

HCID66586742

未命名化合物

PRODUCTS

生成物

结构：CN(CCN1CCOCC1)C(=O)c1cccc(C(=O)Nc2ccc(N3CCCCC3)cc2-c2cc(C(=O)NCc3cccc(C(F)(F)F)c3)ccn2)n1

HCID86705943

未命名化合物

PROCEDURE

实验过程

A solution of 25 mg of N-(3-(trifluoromethyl)benzyl)-2-(2-amino-5-(piperidin-1-yl)phenyl)isonicotinamide 4.1c, 28 mg of pyridine-2,6-dicarboxylic acid, and 4.3 mg of diisopropylethylamine in 1 mL of DMF was treated with 21 mg of HATU. After 2 h the mixture was separated by reverse phase HPLC, eluting with 0.05% TFA in a water/acetonitrile gradient. The isolated monoamide adduct of pyridine-2,6-dicarboxylic acid and 4.1c was dissolved in 2 mL of DMF and treated with 10 mg of N-methyl-2-morpholinoethanamine, 28 mg of diisopropylethylamine, and 23 mg of HATU. After 2 h the product was isolated by reverse phase HPLC. MS (ES, m/z) 730 [M+H]+

WORKUP

后处理

customAfter 2 h the mixture was separated by reverse phase HPLC
washeluting with 0.05% TFA in a water/acetonitrile gradient
dissolutionThe isolated monoamide adduct of pyridine-2,6-dicarboxylic acid and 4.1c was dissolved in 2 mL of DMF
additiontreated with 10 mg of N-methyl-2-morpholinoethanamine, 28 mg of diisopropylethylamine, and 23 mg of HATU
customAfter 2 h the product was isolated by reverse phase HPLC

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-674807ce52eb42dd8e8b4b13563be8ef
来源数据集: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08916569B2
来源说明: uspto-grants-2014_12

反应 SMILES

[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][CH:31]=1)[CH2:6][NH:7][C:8](=[O:28])[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2[CH:20]=[C:19]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:18]=[CH:17][C:16]=2[NH2:27])[CH:10]=1.[N:34]1[C:39]([C:40]([OH:42])=O)=[CH:38][CH:37]=[CH:36][C:35]=1[C:43]([OH:45])=O.[CH:46]([N:49]([CH:52]([CH3:54])C)[CH2:50][CH3:51])(C)[CH3:47].[CH3:55][N:56](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C=[O:83])C>>[CH3:55][N:56]([CH2:47][CH2:46][N:49]1[CH2:52][CH2:54][O:83][CH2:51][CH2:50]1)[C:40]([C:39]1[CH:38]=[CH:37][CH:36]=[C:35]([C:43]([NH:27][C:16]2[CH:17]=[CH:18][C:19]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:20][C:15]=2[C:11]2[CH:10]=[C:9]([C:8](=[O:28])[NH:7][CH2:6][C:5]3[CH:29]=[CH:30][CH:31]=[C:3]([C:2]([F:1])([F:32])[F:33])[CH:4]=3)[CH:14]=[CH:13][N:12]=2)=[O:45])[N:34]=1)=[O:42]