Reaktion #160881

Reaktionsgleichung

Methyl magnesium bromide

solution

4-amino-N-methoxy-N-methyl-7-[(4-methylpiperazin-1-yl)methyl]-5-{4-[({[4-(trifluoromethyl)pyridin-2-yl]amino}-carbonyl)amino]-phenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide

→

title compound

Ausbeute 42.9%

N-(4-{6-acetyl-4-amino-7-[(4-methylpiperazin-1-yl)methyl]pyrrolo[2,1-f][1,2,4]triazin-5-yl}phenyl)-N′-[4-(trifluoromethyl)-pyridin-2-yl]urea

Ausbeute 42.9%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeuntil all starting material had been consumed
2. 2
   TemperaturAfter cooling to rt
3. 3
   Sonstigethe reaction was quenched with methanol
4. 4
   workup.ADDITIONdiluted with 100 mL of EtOAc
5. 5
   Waschenwashed 3× with saturated NH4Cl solution
6. 6
   TrocknenThe organic layer was dried over Na2SO4
7. 7
   Einengenconcentrated
8. 8
   Sonstigepurified by HPLC (10-70% ACN/H2O)

Vorschrift

Methyl magnesium bromide (0.54 mL, 1.63 mmol, in 3.0 M in diethyl ether) was added dropwise to a stirring solution of Example 94 (100.0 mg, 0.163 mmol) in THF (2 mL) at rt. The reaction was heated to 60° C. and allowed to stir overnight (15 hrs) or until all starting material had been consumed as seen by HPLC. After cooling to rt, the reaction was quenched with methanol and diluted with 100 mL of EtOAc and washed 3× with saturated NH4Cl solution. The organic layer was dried over Na2SO4, concentrated and purified by HPLC (10-70% ACN/H2O) to give 37.9 mg (0.07 mmol, 40.9%) of the title compound. 1H-NMR (DMSO-d6). δ 10.88 (s, 1H), 10.19 (s, 1H), 8.57 (d, J=5.4 Hz, 1H), 8.27 (s, 1H), 8.03 (s, 1H), 7.70 (d, J=8.1 Hz, 2H), 7.40-7.35 (m, 3H), 4.17 (s, 2H), 3.08-3.04 (m, 4H), 2.73-2.65 (m, 7H), 2.06 (s, 3H). MS [M+H]+=568; LCMS RT=2.31 min.

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