2-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamoyl)-1-methyl-1H-indol-4-yl acetate → HCID 178487945, Verbindung

HRID 245737

Reaktionsgleichung

Reaktionsgleichung von HRID 245737
[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([C:15](=[O:34])[NH:16][C:17]1[CH:22]=[CH:21][C:20](B3OC(C)(C)C(C)(C)O3)=[CH:19][C:18]=1[O:32][CH3:33])[N:9]2[CH3:14])(=[O:3])[CH3:2].Br[C:36]1[N:37]=[C:38]([C@H:46]2[CH2:51][CH2:50][C@H:49]([N:52]3[CH2:57][CH2:56][N:55]([CH3:58])[CH2:54][CH2:53]3)[CH2:48][CH2:47]2)[N:39]2[CH:44]=[CH:43][N:42]=[C:41]([CH3:45])[C:40]=12>>[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([C:15](=[O:34])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:36]3[N:37]=[C:38]([C@H:46]4[CH2:47][CH2:48][C@H:49]([N:52]5[CH2:53][CH2:54][N:55]([CH3:58])[CH2:56][CH2:57]5)[CH2:50][CH2:51]4)[N:39]4[CH:44]=[CH:43][N:42]=[C:41]([CH3:45])[C:40]=34)=[CH:19][C:18]=1[O:32][CH3:33])[N:9]2[CH3:14])(=[O:3])[CH3:2]

Komponenten

3

Edukt 2

HCID 673637492-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamoyl)-1-methyl-1H-indol-4-yl acetateHCID 178432912HCID 178432912, Verbindung

Produkt 1

HCID 178487945HCID 178487945, Verbindung

Versuchsvorschrift

Reaction of 2-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamoyl)-1-methyl-1H-indol-4-yl acetate (36 mg) and 1-bromo-8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazine (30 mg) according to the procedure described in example 4 step 4c and purification by column chromatography (silica gel; dichloromethane with gradient 0 to 20% methanol (+ few drops ammonia)) gave 2-(2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamoyl)-1-methyl-1H-indol-4-yl acetate. This product was stirred with 7N ammonia in methanol for 1 h by room temperature, concentrated in vacuo, solved in acetonitril and filtered. The filtrate was concentrated in vacuo to give 4-hydroxy-N-(2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide (15 mg)

Aufarbeitung

  1. customdescribed in example 4 step 4c and purification by column chromatography (silica gel; dichloromethane with gradient 0 to 20% methanol (+ few drops ammonia))

Quellen und Nachweise

ORD-Eintrag
ord-1587dbbc61dc416392e9281de3fc062d
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658794B2

Verknüpfte Notizen

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