Sodium Carbonate → 5-(5-Methyl-1H-pyrazol-4-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine

HRID 605905

Reaktionsgleichung

Reaktionsgleichung von HRID 605905
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[C:16]4[N:17]([N:29]=[CH:30][N:31]=4)[C:18](C4C=C(C(N)=O)SC=4)=[CH:19][N:20]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.BrC1N2N=CN=C2C(NC2C=CC(N3CCN(C)CC3)=CC=2)=NC=1.[CH3:56][C:57]1[NH:61][N:60]=[CH:59][C:58]=1B1OC(C)(C)C(C)(C)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>[CH3:56][C:57]1[NH:61][N:60]=[CH:59][C:58]=1[C:18]1[N:17]2[N:29]=[CH:30][N:31]=[C:16]2[C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)=[CH:9][CH:10]=2)=[N:20][CH:19]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 177502703-Methyl-1H-pyrazole-4-boronic acid pinacol esterHCID 575899284-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amideHCID 57590000(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

Produkt 1

HCID 1359004445-(5-Methyl-1H-pyrazol-4-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amineAusbeute 7 %

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)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (132 mg, 0.340 mmol), 5-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (141 mg, 0.68 mmol), Pd(PPh3)4 (98 mg, 0.085 mmol) and 1.5N Na2CO3 (1.81 mL, 2.72 mmol) in dioxane (5.4 mL). The crude product is purified by silica gel column chromatography eluting with 95:5 DCM:NH3 (7M in MeOH) followed by trituration with diethyl ether and petroleum ether to afford the title compound (9 mg, 7%) as a pale green solid. 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 2.27 (3H, s), 2.38-2.49 (7H, m), 3.14 (4H, m), 6.97 (2H, d), 7.70 (1H, s), 7.88 (2H, d), 7.99 and 8.43 (1H, br s), 8.68 (1H, s), 9.71 (1H, s), 12.92 and 12.98 (1H, br s).

Aufarbeitung

  1. customThis compound may be prepared
  2. customThe crude product is purified by silica gel column chromatography
  3. washeluting with 95:5 DCM

Quellen und Nachweise

ORD-Eintrag
ord-b48e5e6f9dbc404d8df6c7d8af45e210
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915256B2

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