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

HRID 1969482Notes

Reaction equation

HRID 1969482 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)[O:23][CH:24]=1.C(=O)(O)[O-].[Na+].O>CN(C=O)C>[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)[O:23][CH:24]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 71315274-(Chloromethyl)-2-(4-chlorophenyl)-1,3-oxazoleHCID 178510490HCID 178510490, compound

Product 1

HCID 442296442-Amino-6-([2-(4-chlorophenyl)-1,3-oxazol-4-yl]methylsulfanyl)-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

250 mg (0.964 mmol) of 2-amino-6-sulfanyl-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile, together with 242 mg (1.060 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-oxazole and 243 mg (2.892 mmol) of sodium bicarbonate, were stirred in 5 ml DMF at room temperature for 1 h. The reaction mixture was added to water, and the resulting precipitate was filtered off and washed with diethyl ether. Drying under reduced pressure gave 53 mg (12% of theory) of the target compound.

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. washwashed with diethyl ether
  3. customDrying under reduced pressure
  4. customgave 53 mg (12% of theory) of the target compound

Sources & evidence

ORD record
ord-1b3615a3962c44198ae831892ede3c3e
Source dataset
uspto-grants-2013_04
Patent number
US08426602B2

Reaction notes

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