Hydrochloric Acid → 2-Chloro-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile

HRID 1630707Notes

Reaction equation

HRID 1630707 reaction equation
N[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[S:14][CH:13]=[N:12][CH:11]=2)[C:5]([C:15]#[N:16])=[C:4]([S:17][CH2:18][C:19]2[N:20]=[C:21]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[S:22][CH:23]=2)[N:3]=1.N([O-])=O.[Na+].[ClH:35]>>[Cl:35][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[S:14][CH:13]=[N:12][CH:11]=2)[C:5]([C:15]#[N:16])=[C:4]([S:17][CH2:18][C:19]2[N:20]=[C:21]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[S:22][CH:23]=2)[N:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 442296432-Amino-6-([2-(4-chlorophenyl)-1,3-thiazol-4-yl]methylsulfanyl)-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile

Product 1

HCID 866542122-Chloro-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile

Conditions

Temperature
0 °C

Procedure

569 mg (1.218 mmol) of 2-amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile are dissolved in 20 ml of concentrated hydrochloric acid, the mixture is cooled to 0° C. and 252 mg (3.655 mmol) of sodium nitrite are added at this temperature. The mixture is stirred at 0° C. for 1 h and then warmed to room temperature and stirred at room temperature overnight. The reaction mixture is purified by preparative HPLC (acetonitrile/water: 10:90→95:5). This gives 445 mg (68% of theory) of the target compound.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred at room temperature overnight
  3. customThe reaction mixture is purified by preparative HPLC (acetonitrile/water: 10:90→95:5)

Sources & evidence

ORD record
ord-abc435c82b354975a2a160c086508562
Source dataset
uspto-grants-2014_07
Patent number
US08791146B2

Reaction notes

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