1,3-Dibromo-5,5-dimethylhydantoin → HCID 178461723, Verbindung

HRID 81212

Reaktionsgleichung

Reaktionsgleichung von HRID 81212
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([CH:17]([C@H:19]4[CH2:24][CH2:23][C@H:22]([CH3:25])[CH2:21][CH2:20]4)[CH3:18])[CH:15]=[N:16][C:12]=3[CH:11]=[C:10]([C:26]#[N:27])[N:9]=2)[CH:5]=[N:6][CH:7]=1.P([O-])([O-])(O)=O.[Na+].[Na+].[Br:35]N1C(C)(C)C(=O)N(Br)C1=O>C1COCC1>[Br:35][C:15]1[N:14]([C@H:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([CH3:25])[CH2:21][CH2:20]2)[CH3:18])[C:13]2[C:8]([C:4]3[CH:5]=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[N:9][C:10]([C:26]#[N:27])=[CH:11][C:12]=2[N:16]=1.[Br:35][C:15]1[N:14]([C@@H:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([CH3:25])[CH2:21][CH2:20]2)[CH3:18])[C:13]2[C:8]([C:4]3[CH:5]=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[N:9][C:10]([C:26]#[N:27])=[CH:11][C:12]=2[N:16]=1

Komponenten

6

Edukt 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 24203Sodium Phosphate, DibasicHCID 178455733HCID 178455733, Verbindung

Produkt 2

HCID 178461723HCID 178461723, VerbindungHCID 178461724HCID 178461724, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Alternatively, racemic 4-(5-chloropyridin-3-yl)-3-[1-(trans-4-methylcyclohexyl)ethyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (Step 2) was resolved into its enantiomers as described in Preparative Example 15.1 and brominated using the conditions described above or using the alternative conditions (disodium hydrogen phosphate and 1,3-dibromo-5,5-dimethylhydantoin in THF at 35° C., described in Example 2.1, Step 1 and Preparative Example 3.1, Step 3) to afford 2-bromo-4-(5-chloropyridin-3-yl)-3-[(1S)-1-(trans-4-methylcyclohexyl)ethyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile and 2-bromo-4-(5-chloropyridin-3-yl)-3-[(1R)-1-(trans-4-methylcyclohexyl)ethyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile.

Quellen und Nachweise

ORD-Eintrag
ord-f3b67a2cc71943fb8f4ca6928a6c431f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846657B2

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