1-Ethylpiperazine → {4-[2-Ethyl-3-(6-methylamino-pyridin-3-ylethynyl)-pyridin-4-yl]-2-fluoro-phenyl}-(4-ethyl-piperazin-1-yl)-methanone

HRID 1529237Notes

Reaction equation

HRID 1529237 reaction equation
[CH2:1]([C:3]1[C:8]([C:9]#[C:10][C:11]2[CH:12]=[N:13][C:14]([NH:17][CH3:18])=[CH:15][CH:16]=2)=[C:7]([C:19]2[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[C:21]([F:28])[CH:20]=2)[CH:6]=[CH:5][N:4]=1)[CH3:2].[CH2:29]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[CH3:30].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O.C(#N)C>[CH2:1]([C:3]1[C:8]([C:9]#[C:10][C:11]2[CH:12]=[N:13][C:14]([NH:17][CH3:18])=[CH:15][CH:16]=2)=[C:7]([C:19]2[CH:27]=[CH:26][C:22]([C:23]([N:34]3[CH2:35][CH2:36][N:31]([CH2:29][CH3:30])[CH2:32][CH2:33]3)=[O:24])=[C:21]([F:28])[CH:20]=2)[CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 791961-EthylpiperazineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 667708384-[2-Ethyl-3-(6-methylamino-pyridin-3-ylethynyl)-pyridin-4-yl]-2-fluoro-benzoic acid

Product 1

HCID 49800793{4-[2-Ethyl-3-(6-methylamino-pyridin-3-ylethynyl)-pyridin-4-yl]-2-fluoro-phenyl}-(4-ethyl-piperazin-1-yl)-methanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound is synthesized according to general procedure GP5 starting from 100 mg (0.28 mmol) 4-[2-Ethyl-3-(6-methylamino-pyridin-3-ylethynyl)-pyridin-4-yl]-2-fluoro-benzoic acid (A-46) using 55 μL (0.33 mmoL) N-ethyl piperazine, 101 mg (0.27 mmol) HATU and 50 μL DIPEA in 1.5 mL DMF. After completion of the reaction, the reaction mixture is filtered and the product is isolated from the obtained solution by RP-HPLC using a H2O/ACN-gradient. Yield: 82 mg (65%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture is filtered
  3. customthe product is isolated from the obtained solution by RP-HPLC

Sources & evidence

ORD record
ord-0eaa7128b2364e62a5082d21adf2b667
Source dataset
uspto-grants-2015_07
Patent number
US09090564B2

Reaction notes

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