5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one → HCID 57345529, Verbindung

HRID 605916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605916
C[N:2]1CCN(C2C=CC(NC3C4N(N=CN=4)C(C4C=C(C(N)=O)SC=4)=CN=3)=CC=2)CC1.Br[C:33]1[N:38]2[N:39]=[CH:40][N:41]=[C:37]2[C:36]([NH:42][C:43]2[CH:48]=[CH:47][C:46]([N:49]3[CH2:54][CH2:53][O:52][CH2:51][CH2:50]3)=[CH:45][CH:44]=2)=[N:35][CH:34]=1.CC1(C)C(C)(C)OB([C:63]2[CH:64]=[C:65]3[C:69](=[CH:70][CH:71]=2)[C:68](=[O:72])[NH:67][CH2:66]3)O1>C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH3:2].[O:52]1[CH2:53][CH2:54][N:49]([C:46]2[CH:47]=[CH:48][C:43]([NH:42][C:36]3[C:37]4[N:38]([N:39]=[CH:40][N:41]=4)[C:33]([C:63]4[CH:64]=[C:65]5[C:69](=[CH:70][CH:71]=4)[C:68](=[O:72])[NH:67][CH2:66]5)=[CH:34][N:35]=3)=[CH:44][CH:45]=2)[CH2:50][CH2:51]1

Komponenten

8

Edukt 3

HCID 219557955-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one2×HCID 575899284-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amideHCID 57589931(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-ylphenyl)amine

Produkt 2

HCID 222AmmoniaHCID 57345529HCID 57345529, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 10340Sodium CarbonateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

This compound may be prepared using methods as described for Compound 6, step 4 using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-yl-phenyl)-amine (1.0 g, 2.67 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one (see description for Compound 79) (1.03 g, 4.01 mmol) and Pd(PPh3)4 (0.77 g, 0.67 mmol) in 1.5M Na2CO3 (14.3 mL) and dioxane (40 mL). Purification by silica gel column chromatography eluting with DCM followed by 96:4 DCM:NH3 (7M in MeOH) affords the title compound (0.895 g, 79%). 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 3.12 (4H, m), 3.79 (4H, m), 4.51 (2H, s), 7.01 (2H, d), 7.84 (1H, d), 7.92 (2H, d), 8.01 (1H, s), 8.09 (1H, d), 8.23 (1H, s), 8.72 (1H, s), 8.73 (1H, s), 10.02 (1H, s). LCMS: Rt 2.51 min (97.8%), m/z (APCI) 428 (M+H)+.

Aufarbeitung

  1. customThis compound may be prepared
  2. customPurification by silica gel column chromatography
  3. washeluting with DCM

Quellen und Nachweise

ORD-Eintrag
ord-70bd2084c58b499f90a95e4b10953d26
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915256B2

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