4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → N-(4-Hydroxybenzyl)-4-[5-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]benzamide

HRID 1924894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1924894
N1(C2C=CC(NC3C4N(C=CN=4)C(C4C=CNC(=O)C=4)=CN=3)=CC=2)CCOCC1.Br[C:31]1[N:36]2[CH:37]=[CH:38][N:39]=[C:35]2[C:34]([NH:40][C:41]2[CH:57]=[CH:56][C:44]([C:45]([NH:47][CH2:48][C:49]3[CH:54]=[CH:53][C:52]([OH:55])=[CH:51][CH:50]=3)=[O:46])=[CH:43][CH:42]=2)=[N:33][CH:32]=1.CC1(C)C(C)(C)OB([C:66]2[CH:67]=[N:68][NH:69][CH:70]=2)O1.CC([O-])(C)C.[Na+]>CN(C=O)C.O.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>[OH:55][C:52]1[CH:53]=[CH:54][C:49]([CH2:48][NH:47][C:45](=[O:46])[C:44]2[CH:56]=[CH:57][C:41]([NH:40][C:34]3[C:35]4[N:36]([CH:37]=[CH:38][N:39]=4)[C:31]([C:66]4[CH:67]=[N:68][NH:69][CH:70]=4)=[CH:32][N:33]=3)=[CH:42][CH:43]=2)=[CH:50][CH:51]=1

Komponenten

7

Edukt 4

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 23676156Sodium t-butoxideHCID 248574474-[8-(4-Morpholin-4-yl-phenylamino)imidazo[1,2-a]pyrazin-5-yl]-1H-pyridin-2-oneHCID 590230564-(5-Bromoimidazo[1,2-a]pyrazin-8-ylamino)-N-(4-hydroxybenzyl)benzamide

Produkt 1

HCID 24857547N-(4-Hydroxybenzyl)-4-[5-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 21962138N,N-Dimethylformamide--water (1/1)Lösungsmittel

Versuchsvorschrift

In the same way as described for Compound 85, step 1, using 4-(5-bromoimidazo[1,2-a]pyrazin-8-ylamino)-N-(4-hydroxybenzyl)benzamide (47 mg, 0.11 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (25 mg, 0.13 mmol), Pd(PPh3)4 (12 mg, 0.011 mmol) and NaOtBu (41 mg, 0.43 mmol) in DMF/water (3:1). The crude residue is chromatographed on silica gel, eluting with petrol:EtOAc (50:50 followed by 0:100) and then EtOAc:MeOH (95:5). The fractions containing the desired product are combined and evaporated, to afford the title compound as a solid. HPLC (254 nm): Rt 2.38 min (90.9%); m/z (APCI) 426 (M+H)+.

Aufarbeitung

  1. customThe crude residue is chromatographed on silica gel
  2. washeluting with petrol:EtOAc (50:50 followed by 0:100)
  3. additionThe fractions containing the desired product
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-50ce1fdb7b1d4ac0828e0c9a529be500
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178530B2

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