Diisopropylethylamine → HCID 49801084, compound

HRID 1529239Notes

Reaction equation

HRID 1529239 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[C:11]([CH2:26][CH3:27])=[N:12][CH:13]=[CH:14][C:15]=2[C:16]2[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[C:18]([F:25])[CH:17]=2)=[CH:4][CH:3]=1.[CH:28]1([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH2:30][CH2:29]1.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>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[C:11]([CH2:26][CH3:27])=[N:12][CH:13]=[CH:14][C:15]=2[C:16]2[CH:24]=[CH:23][C:19]([C:20]([N:34]3[CH2:35][CH2:36][N:31]([CH:28]4[CH2:30][CH2:29]4)[CH2:32][CH2:33]3)=[O:21])=[C:18]([F:25])[CH:17]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 47420041-CyclopropylpiperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58235232HCID 58235232, compound

Product 1

HCID 49801084HCID 49801084, compound

Reagents, catalysts & solvents 2

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

Procedure

The title compound is synthesized according to general procedure GP5 starting from 120 mg (0.33 mmol) 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-fluoro-benzoic acid (A-38) using 63 mg (0.50 mmoL) N-cyclopropyl piperazine, 139 mg (0.37 mmol) HATU and 96 μL DIPEA in 1.2 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: 30 mg (20%).

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-0f4824244e5d44eea0c55aa366883693
Source dataset
uspto-grants-2015_07
Patent number
US09090564B2

Reaction notes

Loading…