Sodium Bicarbonate → HCID 44229642, compound

HRID 1969480Notes

Reaction equation

HRID 1969480 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[N:11]=[CH:12][S: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)[O: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[N:11]=[CH:12][S: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)[O:23][CH:24]=2)[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 71315274-(Chloromethyl)-2-(4-chlorophenyl)-1,3-oxazoleHCID 178510492HCID 178510492, compound

Product 1

HCID 44229642HCID 44229642, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

90 mg (about 0.298 mmol) of 2-amino-6-sulfanyl-4-(1,3-thiazol-4-yl)pyridine-3,5-dicarbonitrile, together with 87 mg (0.382 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-oxazole and 88 mg (1.041 mmol) of sodium bicarbonate, were stirred in 20 ml DMF at room temperature overnight. The reaction mixture was purified by preparative HPLC (acetonitrile/water: 10:90→95:5, 0.1% TFA added). This gave 37 mg (24% of theory) of the target compound.

Workup

  1. customThe reaction mixture was purified by preparative HPLC (acetonitrile/water: 10:90→95:5, 0.1% TFA added)

Sources & evidence

ORD record
ord-23f543616d6c449596b5ac8aeb3451f2
Source dataset
uspto-grants-2013_04
Patent number
US08426602B2

Reaction notes

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