Dichloromethane → N-{3-[2-(3-Acetylamino-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-2,2-dimethyl-propionamide

HRID 1262136

Reaktionsgleichung

Reaktionsgleichung von HRID 1262136
[CH3:1][C:2]([CH3:24])([CH3:23])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[N:20]3[C:15]([CH:16]=[N:17][C:18](SC)=[N:19]3)=[CH:14][CH:13]=2)[CH:7]=1)=[O:4].CSC1N=CC2=CC=C([C:36]3[CH:37]=[C:38]([NH2:42])[CH:39]=[CH:40][CH:41]=3)N2N=1.C(Cl)Cl.[CH2:46]([N:48](CC)CC)[CH3:47].CC(C)(C)C(Cl)=[O:56]>>[C:46]([NH:48][C:36]1[CH:37]=[C:38]([NH:42][C:18]2[N:17]=[CH:16][C:15]3=[CH:14][CH:13]=[C:12]([C:8]4[CH:7]=[C:6]([NH:5][C:3](=[O:4])[C:2]([CH3:24])([CH3:23])[CH3:1])[CH:11]=[CH:10][CH:9]=4)[N:20]3[N:19]=2)[CH:39]=[CH:40][CH:41]=1)(=[O:56])[CH3:47]

Komponenten

6

Edukt 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 667116972,2-Dimethyl-N-[3-(2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-propionamideHCID 667126823-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenylamine

Produkt 1

HCID 66712052N-{3-[2-(3-Acetylamino-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-2,2-dimethyl-propionamide

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2,2-Dimethyl-N-[3-(2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-propionamide. 3-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenylamine (0.200 g, 0.780 mmol) was dissolved in Methylene chloride (10.0 mL, 156 mmol) and cooled to 0° C. Triethylamine (0.130 mL, 0.936 mmol) was added followed by 2,2-Dimethylpropanoyl chloride (0.106 mL, 0.858 mmol). The reaction mixture was allowed to warm to rt. LCMS after 30 min indicated mass of title compound. Reaction mixture was washed with water, dried over MgSO4, filtered, and concentrated. HPLC rt=3.436, purity=90%, LCMS=341.2 (M+H).

Aufarbeitung

  1. temperatureto warm to rt

Quellen und Nachweise

ORD-Eintrag
ord-8331ea240a1343d298aa48c4930429c6
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

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