Hydrochloric Acid → N-methyl-N-[(1R)-1-phenylethyl]-2-(1-piperazinyl)-5-thiazole-carboxamide

HRID 2043722Notes

Reaction equation

HRID 2043722 reaction equation
[CH3:1][N:2]([C@@H:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:24])[C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:4].ClCCl.Cl>CO.CCOCC>[CH3:1][N:2]([C@@H:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:24])[C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)=[N:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 674613901,1-Dimethylethyl 4-[5-[[methyl[(1R)-1-phenylethyl]amino]carbonyl]-2-thiazolyl]-1-piperazinecarboxylate2×

Product 1

HCID 67461626N-methyl-N-[(1R)-1-phenylethyl]-2-(1-piperazinyl)-5-thiazole-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1,1-Dimethylethyl 4-[5-[[methyl[(1R)-1-phenylethyl]amino]carbonyl]-2-thiazolyl]-1-piperazinecarboxylate (i.e. the product of Example 4, Step C) (0.75 g, 1.7 mmol) in 10 mL of methanol and 10 mL of dichloromethane was treated with 15 mL of 1 N HCl in ether. The reaction mixture was stirred at ambient temperature overnight, concentrated under reduced pressure, dissolved in water and brine, basified with 1. N aqueous NaOH solution and extracted with dichloromethane. The extract was dried over MgSO4 and concentrated under reduced pressure to give 0.48 g of the title compound as a yellow oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutiondissolved in water
  3. extractionN aqueous NaOH solution and extracted with dichloromethane
  4. dry with materialThe extract was dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-377b217f188d48b699c9f09725caa80a
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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