Ethyl bromopyruvate → HCID 82030624, compound

HRID 1895387Notes

Reaction equation

HRID 1895387 reaction equation
ClC1C=CC(NC(N)=S)=NC=1.C(OC(=O)C(=O)CBr)C.[CH2:21]([O:23][C:24]([C:26]1[N:27]=[C:28]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][N:33]=2)[S:29][CH:30]=1)=[O:25])[CH3:22]>CO.CO.O1CCCC1.[OH-].[Na+].O>[CH2:21]([O:23][C:24]([C:26]1[N:27]=[C:28]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][N:33]=2)[S:29][CH:30]=1)=[O:25])[CH3:22].[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([NH:31][C:28]2[S:29][CH:30]=[C:26]([C:24]([OH:25])=[O:23])[N:27]=2)=[N:33][CH:34]=1

Participants

9

Reactant 3

HCID 66144Ethyl bromopyruvateHCID 7175947(5-Chloro-pyridin-2-yl)-thioureaHCID 86661618HCID 86661618, compound

Product 2

HCID 82030624HCID 82030624, compoundHCID 86661618HCID 86661618, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2-(5-Chloro-pyridin-2-ylamino)-thiazole-4-carboxylic acid ethyl ester (1.0 g) was prepared according to General Procedure C using (5-chloro-pyridin-2-yl)-thiourea (1.0 g) and 3-bromo-2-oxo-propionic acid ethyl ester (1.07 g) in methanol (15 mL). The crude product was washed with a dichloromethane:hexane (1:1, 200 mL) solution to give a substantially pure product. 2-(5-Chloro-pyridin-2-ylamino)-thiazole-4-carboxylic acid (76 mg) was prepared according to General Procedure C using 2-(5-chloro-pyridin-2-ylamino)-thiazole-4-carboxylic acid ethyl ester (100 mg) in methanol:tetrahydrofuran (1:1, 2 mL) and 2N sodium hydroxide in water (0.5 mL). The crude product was used in subsequent steps without further purification.

Workup

  1. washThe crude product was washed with a dichloromethane:hexane (1:1, 200 mL) solution
  2. customto give a substantially pure product
  3. customThe crude product was used in subsequent steps without further purification

Sources & evidence

ORD record
ord-6220f9aae1774356aacf3c1acef9dbea
Source dataset
uspto-grants-2013_08
Patent number
US08513430B2

Reaction notes

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