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

HRID 1500098Notes

Reaction equation

HRID 1500098 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

370 mg (1.427 mmol) of 2-amino-6-sulphanyl-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile, 383 mg (1.570 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 359 mg of sodium bicarbonate are stirred in 7 ml of DMF for 1 hour. 150 ml of acetonitrile and 100 ml of water are added to the reaction mixture, and the precipitated solid is filtered off and dried under high vacuum. This gives 569 mg (85% of theory) of the target compound.

Workup

  1. filtrationthe precipitated solid is filtered off
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-75620066849a400288df8e3b4cc99ddc
Source dataset
uspto-grants-2015_12
Patent number
US09205077B2

Reaction notes

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