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 1969475Notes

Reaction equation

HRID 1969475 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

At 0° C., 50 mg (0.107 mmol) of 2-amino-6-([2-(4-chlorophenyl)-1,3-thiazol-4-yl]methylsulfanyl)-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile were dissolved in 1.5 ml of concentrated hydrochloric acid, and 22 mg (0.321 mmol) of sodium nitrite were added. The mixture was stirred initially at 0° C. for one hour and then at room temperature overnight. Purification of the reaction mixture was by preparative HPLC (acetonitrile/water: 10:90→95:5, 0.1% TFA added). This gave 9 mg (17% of theory) of the target compound.

Workup

  1. customat room temperature
  2. customovernight
  3. customPurification of the reaction mixture
  4. additionwas by preparative HPLC (acetonitrile/water: 10:90→95:5, 0.1% TFA added)

Sources & evidence

ORD record
ord-04709ee706434746be9d9701e4412c57
Source dataset
uspto-grants-2013_04
Patent number
US08426602B2

Reaction notes

Loading…