Sodium Bicarbonate → HCID 67348744, compound

HRID 1969488Notes

Reaction equation

HRID 1969488 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=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+]>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=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

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 178510487HCID 178510487, compound

Product 1

HCID 67348744HCID 67348744, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

70 mg (0.271 mmol) of 2-amino-6-sulfanyl-4-thiophen-2-ylpyridine-3,5-dicarbonitrile, together with 79 mg (0.325 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 91 mg (1.084 mmol) of sodium bicarbonate, were stirred in 2 ml DMF at room temperature overnight. The reaction mixture was filtered and the filtrate was purified by preparative HPLC (Chromasil, water/acetonitrile—without acid). This gave 94 mg (71% of theory) of the target compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was purified by preparative HPLC (Chromasil, water/acetonitrile—without acid)

Sources & evidence

ORD record
ord-4c58746da0fe416b979157d695b65d61
Source dataset
uspto-grants-2013_04
Patent number
US08426602B2

Reaction notes

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