Diisopropylethylamine → HCID 49801085, compound

HRID 1529240Notes

Reaction equation

HRID 1529240 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.[O:28]1[CH2:33][CH2:32][CH:31]([N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]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.CO>[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:37]3[CH2:36][CH2:35][N:34]([CH:31]4[CH2:32][CH2:33][O:28][CH2:29][CH2:30]4)[CH2:39][CH2:38]3)=[O:21])=[C:18]([F:25])[CH:17]=2)=[CH:4][CH:3]=1

Participants

7

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 219423151-(Oxan-4-yl)piperazineHCID 58235232HCID 58235232, compound

Product 1

HCID 49801085HCID 49801085, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22242641Methanol--water (1/1)Solvent

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 181 mg (1.06 mmoL) 1-tetrahydro-pyran-4-yl piperazine, 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/MeOH-gradient. Yield: 90 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-04370fb485974654837674042b592c91
Source dataset
uspto-grants-2015_07
Patent number
US09090564B2

Reaction notes

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