Tetrafluoroborate → HCID 86712345, Verbindung

HRID 592482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 592482
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=2)[N:3]=1.[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1([C:30]([NH2:32])=[O:31])[CH2:29][CH2:28]1)#[CH:20].F[B-](F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:18][N:16]1[CH:17]=[C:13]([NH:12][C:4]2[N:3]=[C:2]([C:20]#[C:19][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3([C:30]([NH2:32])=[O:31])[CH2:29][CH2:28]3)[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=2)[CH:14]=[N:15]1

Komponenten

8

Edukt 4

HCID 26255TetrafluoroborateHCID 81531DiisopropylethylamineHCID 867122761-(2-Ethynylphenyl)cyclopropanecarboxamideHCID 867123374-Chloro-N-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)pyrimidin-2-amine

Produkt 1

HCID 86712345HCID 86712345, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a degassed mixture of 4-chloro-N-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)pyrimidin-2-amine A74 (0.178 g, 0.640 mmol), 1-(2-ethynylphenyl)cyclopropanecarboxamide K6 (0.172 g, 0.928 mmol), PdCl2(PPh3)2 (0.005 g, 0.007 mmol), t-Bu3PH.BF4 (0.005 g, 0.02 mmol) and copper(I) iodide (0.003 g, 0.02 mmol) in DMF (8.0 mL) was added DIPEA (0.33 mL, 1.9 mmol). The mixture was heated in the microwave for 2×20 minutes at 100° C. before being concentrated under reduced pressure. Purification by silica gel column chromatography (Isolera, 0-100% EtOAc petroleum benzine 40-60° C. then 0-20% MeOH in EtOAc) gave the title compound A75 (0.120 g, 44%). LCMS-D: rt 3.30 min; m/z 427.2 [M+H]+.

Aufarbeitung

  1. concentrationbefore being concentrated under reduced pressure
  2. customPurification by silica gel column chromatography (Isolera, 0-100% EtOAc petroleum benzine 40-60° C.

Quellen und Nachweise

ORD-Eintrag
ord-a2ecf98f18cf4176baf55c36d3169af9
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238644B2

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