Sodium Carbonate → HCID 135979591, Verbindung

HRID 605940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605940
CN1CCN(C2C=CC(NC3C4[N:17]([N:29]=[CH:30]N=4)[C:18]([C:21]4C=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][C:44]=2[F:55])=[N:35][CH:34]=1.CC1(C)C(C)(C)OB(C2C=NNC=2)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>[F:55][C:44]1[CH:45]=[C:46]([N:49]2[CH2:54][CH2:53][O:52][CH2:51][CH2:50]2)[CH:47]=[CH:48][C:43]=1[NH:42][C:36]1[C:37]2[N:38]([N:39]=[CH:40][N:41]=2)[C:33]([C:21]2[CH:30]=[N:29][NH:17][CH:18]=2)=[CH:34][N:35]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 575899284-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amideHCID 57590026HCID 57590026, Verbindung

Produkt 1

HCID 135979591HCID 135979591, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 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)-(2-fluoro-4-morpholin-4-yl-phenyl)-amine (80 mg, 0.203 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (79 mg, 0.406 mmol), and Pd(PPh3)4 (59 mg, 0.051 mmol) in 1.5N Na2CO3 (1.09 mL, 1.62 mmol) and dioxane (3.25 mL). The reaction mixture is purified by silica gel column chromatography eluting with 97:3 DCM:NH3 (7M in MeOH). The fractions containing the product are combined and evaporated in vacuo to afford a solid which is triturated with diethyl ether and petroleum ether to yield the title compound (29 mg, 38%). LCMS: Rt 2.90 min (96%).

Aufarbeitung

  1. customThis compound may be prepared
  2. customThe reaction mixture is purified by silica gel column chromatography
  3. washeluting with 97:3 DCM
  4. additionThe fractions containing the product
  5. customevaporated in vacuo
  6. customto afford a solid which
  7. customis triturated with diethyl ether and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-816328779faf407089631204f29c7e69
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915256B2

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