Acetonitrile → 2-Amino-6-([2-(4-chlorophenyl)-1,3-thiazol-4-yl]methylsulfanyl)-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile

HRID 1969481Notes

Reaction equation

HRID 1969481 reaction equation
[NH2:1][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]([SH:17])[N:3]=1.Cl[CH2:19][C:20]1[N:21]=[C:22]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[S:23][CH:24]=1.C(=O)(O)[O-].[Na+].C(#N)C>CN(C=O)C.O>[NH2:1][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][CH2:19][C:20]2[N:21]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[S:23][CH:24]=2)[N:3]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 178510490HCID 178510490, compound

Product 1

HCID 442296432-Amino-6-([2-(4-chlorophenyl)-1,3-thiazol-4-yl]methylsulfanyl)-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

765 mg (2.950 mmol) of 2-amino-6-sulfanyl-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile, together with 792 mg (3.245 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 744 mg (8.850 mmol) of sodium bicarbonate, were stirred in 15 ml DMF at room temperature for 1 h. The reaction mixture was added to 150 ml of acetonitrile, and 100 ml of water were then added. The resulting precipitate was filtered off and washed initially with a little acetonitrile and then with diethyl ether. Drying under reduced pressure gave 889 mg (53% of theory) of the target compound.

Workup

  1. additionwere then added
  2. filtrationThe resulting precipitate was filtered off
  3. washwashed initially with a little acetonitrile
  4. customDrying under reduced pressure
  5. customgave 889 mg (53% of theory) of the target compound

Sources & evidence

ORD record
ord-00fa1acd5a354b968d2d32d017872982
Source dataset
uspto-grants-2013_04
Patent number
US08426602B2

Reaction notes

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