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

HRID 1852819

Reaction equation

HRID 1852819 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-4b2fdae980dc41d2870b17120e338d9c
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Linked notes

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