Sodium Carbonate → HCID 86636293, Verbindung

HRID 541937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541937
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].Br[C:9]1[CH:10]=[C:11]2[CH:29]=[C:27]([CH:28]=1)[NH:26][C:25]1=[N:30][C:21](=[C:22]([Cl:31])[CH:23]=[N:24]1)[NH:20][C:19]1=[CH:32][C:15](=[CH:16][CH:17]=[CH:18]1)[O:14][CH2:13][CH2:12]2.CC1(C)C(C)(C)OB([C:41]2[CH:46]=[CH:45][N:44]=[C:43]([N:47]3[CH2:52][CH2:51][N:50](C(OC(C)(C)C)=O)[CH2:49][CH2:48]3)[CH:42]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:31][C:22]1[CH:23]=[N:24][C:25]2[NH:26][C:27]3[CH:28]=[C:9]([C:41]4[CH:46]=[CH:45][N:44]=[C:43]([N:47]5[CH2:48][CH2:49][NH:50][CH2:51][CH2:52]5)[CH:42]=4)[CH:10]=[C:11]([CH:29]=3)[CH2:12][CH2:13][O:14][C:15]3[CH:32]=[C:19]([NH:20][C:21]=1[N:30]=2)[CH:18]=[CH:17][CH:16]=3

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 179989162-(4-tert-Butoxycarbonylpiperazin-1-yl)pyridine-4-boronic acid, pinacol esterHCID 6689746719-Bromo-6-chloro-14-oxa-2,4,8,23-tetraazatetracyclo[15.3.1.1(3,7).1(9,13)]tricosa-1(21),3(23),4,6,9(22),10,12,17,19-nonaene trifluoroacetate

Produkt 1

HCID 86636293HCID 86636293, VerbindungAusbeute 40,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A solution of 19-bromo-6-chloro-14-oxa-2,4,8,23-tetraazatetracyclo[15.3.1.1(3,7).1(9,13)]tricosa-1(21),3(23),4,6,9(22),10,12,17,19-nonaene trifluoroacetate (40 mg, 96 μmol), tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]piperazine-1-carboxylate (45 mg, 0.12 mmol), and 2 M sodium carbonate (0.14 mL, 0.29 mmol) in toluene (0.36 mL) and ethanol (0.36 mL) was degassed with nitrogen, treated with tetrakis(triphenylphosphine)palladium(O) (8 mg, 6.7 μmol), and heated at 85° C. for 9 h. The reaction mixture was concentrated, stirred in TFA (1.5 mL) for 30 min, concentrated, and purified by preparative LCMS to give the desired product (11 mg, 14%) as a white solid. LCMS for C27H27ClN7O (M+H)+: m/z=500.0. 1H NMR (300 MHz, DMSO-d6): δ 9.59 (s, 1H), 9.25 (s, 1H), 8.88 (br s, 2H), 8.21-8.18 (m, 2H), 8.00 (s, 1H), 7.67 (s, 1H), 7.35-7.29 (m, 2H), 7.25-7.16 (m, 2H), 7.00-6.80 (m, 3H), 4.55 (br s, 2H), 3.80 (br s, 4H), 3.21 (br s, 4H), 2.82 (br s, 2H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. concentrationconcentrated
  3. custompurified by preparative LCMS

Quellen und Nachweise

ORD-Eintrag
ord-7e31e2a979b1417b936a1d76db809623
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871753B2

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