Water → HCID 68784936, Verbindung

HRID 2093590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2093590
C(=O)([O-])[O-].[Na+].[Na+].[C:7](B(O)O)([CH3:9])=[CH2:8].Cl[C:14]1[N:19]=[C:18]([N:20]2[CH2:25][CH2:24][CH:23]([CH2:26][NH:27][C:28](=[O:49])[C:29]3[CH:34]=[CH:33][C:32]([C:35]4[O:36][C:37]5[C:43]([CH:44]([CH3:46])[CH3:45])=[CH:42][C:41]([C:47]#[N:48])=[CH:40][C:38]=5[N:39]=4)=[CH:31][CH:30]=3)[CH2:22][CH2:21]2)[CH:17]=[CH:16][N:15]=1.O>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].C(O)C>[C:47]([C:41]1[CH:42]=[C:43]([CH:44]([CH3:46])[CH3:45])[C:37]2[O:36][C:35]([C:32]3[CH:33]=[CH:34][C:29]([C:28]([NH:27][CH2:26][CH:23]4[CH2:24][CH2:25][N:20]([C:18]5[CH:17]=[CH:16][N:15]=[C:14]([C:7]([CH3:9])=[CH2:8])[N:19]=5)[CH2:21][CH2:22]4)=[O:49])=[CH:30][CH:31]=3)=[N:39][C:38]=2[CH:40]=1)#[N:48]

Komponenten

8

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10855372(Prop-1-en-2-yl)boronic acidHCID 25169790N-{[1-(2-Chloropyrimidin-4-yl)piperidin-4-yl]methyl}-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzamide

Produkt 1

HCID 68784936HCID 68784936, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Sodium carbonate (120 uL, 2M aqueous), isopropenylboronic acid (21 mg), and N-{[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]methyl}-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzamide (31 mg, EXAMPLE 7) were dissolved in toluene (2.1 ml), water (0.6 ml) and ethanol (0.3 ml). To this solution was added palladium tetrakis(triphenylphosphine) (10 mg). The mixture was heated to 150° C. for 25 min in a microwave reactor. Upon cooling, the mixture was then concentrated in vacuo, taken up in dichloromethane, and purified via flash chromatography on a Biotage Horizon, 25 M column, eluting with 10 column volumes of ethyl acetate to provide the title compound (19 mg, 61%). Mass spectrum (ESI) 521.4 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.34 (d, J=8.5 Hz, 2H), 8.23 (d, J=6.2 Hz, 1H), 7.95 (d, J=8.0 Hz, 3H), 7.52 (s, 1H), 6.38 (d, J=6.2 Hz, 1H), 6.31 (t, J=6.0 Hz, 1H), 6.30 (s, 1H), 5.41 (s, 1H), 4.52 (d, J=8.7 Hz, 2H), 3.46 (m, 3H), 2.91 (t, J=12.4 Hz, 2H), 2.19 (s, 3H), 2.00 (m, 2H), 1.90 (d, J=12.2 Hz, 2H), 1.46 (d, J=7.0, 6H), 1.33 (m, 2H).

Aufarbeitung

  1. temperatureUpon cooling
  2. concentrationthe mixture was then concentrated in vacuo
  3. custompurified via flash chromatography on a Biotage Horizon, 25 M column
  4. washeluting with 10 column volumes of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3ae416a5af224897a7014aee075d59bd
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445480B2

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