Diisopropylethylamine → HCID 49801367, compound

HRID 1529244Notes

Reaction equation

HRID 1529244 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.CN([C:31]([O:35]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:52][CH2:53][N:54]([CH:58](C)C)C(C)C.O.C(#N)C>CN(C=O)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:54]([CH2:53][CH2:52][O:35][CH3:31])[CH3:58])=[O:21])=[C:18]([F:25])[CH:17]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18373917Acetonitrile--water (1/1)HCID 58235232HCID 58235232, compound

Product 1

HCID 49801367HCID 49801367, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound is synthesized according to general procedure GP5 starting from 320 mg (0.89 mmol) 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-fluoro-benzoic acid (A-38) using 95 mg (1.06 mmoL) 2-methoxy methylamine, 370 mg (0.97 mmol) HATU and 258 μL DIPEA in 3 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: 130 mg (34%).

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-e0273731b3e149d59134243d1eae0816
Source dataset
uspto-grants-2015_07
Patent number
US09090564B2

Reaction notes

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