Sodium Bicarbonate → HCID 68586550, compound

HRID 242173Notes

Reaction equation

HRID 242173 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][N:11]=2)[C:5]([C:20]#[N:21])=[C:4]([SH:22])[N:3]=1.Cl[CH2:24][C:25]1[N:26]=[C:27]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[S:28][CH:29]=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[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][N:11]=2)[C:5]([C:20]#[N:21])=[C:4]([S:22][CH2:24][C:25]2[N:26]=[C:27]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[S:28][CH:29]=2)[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 178510484HCID 178510484, compound

Product 1

HCID 68586550HCID 68586550, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

23 mg of the crude product from example 29A are dissolved in 0.7 ml of dry DMF, and 11 mg (0.04 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 12 mg (0.14 mmol) of sodium bicarbonate are added. The reaction mixture is stirred at RT for 8 h. The mixture is then poured into 2 ml of saturated aqueous sodium bicarbonate solution, and the aqueous phase is extracted three times with in each case 4 ml of ethyl acetate. The combined organic phases are dried over magnesium sulphate, and the solvent is removed on a rotary evaporator. The residue is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Workup

  1. extractionthe aqueous phase is extracted three times with in each case 4 ml of ethyl acetate
  2. dry with materialThe combined organic phases are dried over magnesium sulphate
  3. customthe solvent is removed on a rotary evaporator
  4. customThe residue is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Sources & evidence

ORD record
ord-b0191a07182c46e181115d98d7667536
Source dataset
uspto-grants-2014_02
Patent number
US08653109B2

Reaction notes

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