Dichloromethane → HCID 60209264, Verbindung

Reaktionsgleichung

[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[CH:8]=2)=[C:4]([F:22])[CH:3]=1.COC1C=CC(CNC2N=CN=C(OC3C=CC(N[C:45]([NH:47][C:48](=[O:57])[CH2:49][C:50]4[CH:55]=[CH:54][C:53]([F:56])=[CH:52][CH:51]=4)=[O:46])=CC=3F)C=2)=CC=1.C(Cl)[Cl:62]>>[ClH:62].[CH3:19][N:17]([CH3:18])[CH2:16][CH2:15][CH2:14][NH:13][C:9]1[CH:8]=[C:7]([CH2:6][C:5]2[CH:20]=[CH:21][C:2]([NH:1][C:45]([NH:47][C:48](=[O:57])[CH2:49][C:50]3[CH:55]=[CH:54][C:53]([F:56])=[CH:52][CH:51]=3)=[O:46])=[CH:3][C:4]=2[F:22])[CH:12]=[CH:11][N:10]=1

Komponenten

Edukt 3

HCID 6344Dichloromethane

HCID 115698931-(4-(6-(4-Methoxybenzylamino)pyrimidin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea2×

HCID 59852916N3-[4-[(4-Amino-2-fluorophenyl)methyl]-2-pyridinyl]-N1,N1-dimethyl-1,3-propanediamine

Produkt 1

HCID 60209264HCID 60209264, VerbindungAusbeute 14 %

Versuchsvorschrift

To a solution of 4-(4-amino-2-fluorobenzyl)-N-(3-(dimethylamino)propyl)pyridin-2-amine (30 mg, 0.1 mmol) in DCM (2 mL) was added a solution of 2-(4-fluorophenyl)acetyl isocyanate (Compound D of Example 11, 0.347 M in toluene, 0.25 mL). The mixture was stirred at room temperature for 0.5 h before it was quenched with MeOH. The solution was concentrated in vacuo and the residue was purified by prep. HPLC. The desired fractions were collected and concentrated in vacuo. The residue was dissolved in MeOH and polymer bound diethylene triamine (50 mg) was added to remove trifluoroacetic acid. After filtration and concentration, the residue was converted to a hydrochloride salt by the addition of 1 N HCl (0.5 mL) and lyophilized to give 1-(4-((2-(3-(dimethylamino)propylamino)pyridin-4-yl)methyl)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea hydrochloride (8.0 mg, 14% yield). MS(ESI+): m/z 482.24 (M+H)+.