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

HRID 81212

Reaction equation

HRID 81212 reaction equation
[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

Participants

6

Reactant 3

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

Product 2

HCID 178461723HCID 178461723, compoundHCID 178461724HCID 178461724, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Sources & evidence

ORD record
ord-f3b67a2cc71943fb8f4ca6928a6c431f
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Linked notes

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