Trifluoroacetic acid → 4-(1-Phenylcyclopropylamino)-6-(3-(piperazin-1-yl)phenylamino)nicotinamide

HRID 513285

Reaktionsgleichung

Reaktionsgleichung von HRID 513285
Cl[C:2]1[CH:10]=[C:9]([NH:11][C:12]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:14][CH2:13]2)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:23]=[C:24]([N:28]2[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].C(O)(C(F)(F)F)=O>O1CCOCC1.C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:15]1([C:12]2([NH:11][C:9]3[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=[C:2]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([N:28]5[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]5)[CH:23]=4)[CH:10]=3)[CH2:14][CH2:13]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

9

Edukt 5

HCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 22330182tert-Butyl 4-(3-aminophenyl)piperazine-1-carboxylateHCID 866645416-Chloro-4-(1-phenylcyclopropylamino)nicotinamide

Produkt 1

HCID 569687044-(1-Phenylcyclopropylamino)-6-(3-(piperazin-1-yl)phenylamino)nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 6-chloro-4-(1-phenylcyclopropylamino)nicotinamide (150 mg, 0.522 mmol) in p-Dioxane (4.5 mL) was added tert-butyl 4-(3-aminophenyl)piperazine-1-carboxylate (174 mg, 0.626 mmol), Pd(OAc)2 (23 mg, 0.104 mmol), BINAP (65 mg, 0.104 mmol) and Cs2CO3 (510 mg, 1.566 mmol). After stirred at 80° C. for 15 h, it was concentrated to give crude residue, which was then treated with TFA in DCM, 30 min later, the solution was concentrated, the residue was purified by preparative HPLC to give 4-(1-phenylcyclopropylamino)-6-(3-(piperazin-1-yl)phenylamino)nicotinamide. MS found for C25H28N6O as (M+H)+ 429.4. UV: λ=254.6 nm. 1H NMR: (CD3OD) δ 8.17 (s, 1H), 7.31-7.20 (m, 4H), 7.13 (m, 2H), 6.95 (dd, J=8.0, 2.0 Hz, 1H), 6.79 (t, J=2.0 Hz, 1H), 6.60 (dd, J=7.2, 2.0 Hz, 1H), 6.12 (s, 1H), 3.34 (m, 8H), 1.36 (m, 4H) ppm.

Aufarbeitung

  1. concentrationit was concentrated
  2. customto give crude residue, which
  3. concentrationthe solution was concentrated
  4. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-1a1cca8c149e4bdda16d8f9adfe98a25
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102625B2

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