Sodium Hydroxide → HCID 86661619, compound

HRID 1895401Notes

Reaction equation

HRID 1895401 reaction equation
ClC1C=CC(NC(N)=S)=NC=1.C(OC(=O)C(Cl)C=O)C.[CH2:21]([O:23][C:24]([C:26]1[S:30][C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][N:33]=2)=[N:28][CH:27]=1)=[O:25])[CH3:22].[OH-].[Na+]>C1C=CC=CC=1.CO.O1CCCC1>[CH2:21]([O:23][C:24]([C:26]1[S:30][C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][N:33]=2)=[N:28][CH:27]=1)=[O:25])[CH3:22].[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([NH:31][C:29]2[S:30][C:26]([C:24]([OH:25])=[O:23])=[CH:27][N:28]=2)=[N:33][CH:34]=1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 118030Ethyl (chloroformyl)acetateHCID 7175947(5-Chloro-pyridin-2-yl)-thioureaHCID 86661619HCID 86661619, compound

Product 2

HCID 86661619HCID 86661619, compoundHCID 86661620HCID 86661620, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(5-Chloro-pyridin-2-ylamino)-thiazole-5-carboxylic acid ethyl ester (1.0 g) was prepared according to General Procedure C using (5-chloro-pyridin-2-yl)-thiourea (938 mg) and 2-chloro-3-oxo-propionic acid ethyl ester (900 mg) in benzene (15 mL). The crude product was washed with dichloromethane:hexane (1:1, 200 mL) solution to give a substantially pure product. 2-(5-Chloro-pyridin-2-ylamino)-thiazole-5-carboxylic acid (663 mg) was prepared according to General Procedure C using 2-(5-Chloro-pyridin-2-ylamino)-thiazole-5-carboxylic acid ethyl ester (1.0 g) in methanol:tetrahydrofuran:2N NaOH (1:1:1, 6 mL). The crude product was used in a subsequent step without further purification.

Workup

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

Sources & evidence

ORD record
ord-cd8a1da9b18e4f8b9e35e94534194b8b
Source dataset
uspto-grants-2013_08
Patent number
US08513430B2

Reaction notes

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