Hydrochloric Acid → 2-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chlorophenyl)ethyl]amide

HRID 1009195Notes

Reaction equation

HRID 1009195 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[O:25])[NH:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[N:13]=1)(C)(C)C.Cl>CO.O1CCOCC1>[Cl:24][C:20]1[CH:19]=[C:18]([CH2:17][CH2:16][NH:15][C:14]([C:12]2[N:13]=[C:9]([CH2:8][NH2:7])[S:10][CH:11]=2)=[O:25])[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67304673{4-[2-(3-Chlorophenyl)ethylcarbamoyl]thiazol-2-ylmethyl}carbamic acid tert-butyl ester

Product 1

HCID 577870612-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chlorophenyl)ethyl]amide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of {4-[2-(3-Chlorophenyl)ethylcarbamoyl]thiazol-2-ylmethyl}carbamic acid tert-butyl ester (0.73 g, 1.8 mmol) in methanol (10 mL) was added HCl in dioxane (4M solution, 10 mL). The mixture stirred for 12 hours. The methanol and dioxane were removed in vacuo and the resulting solid was vigorously mixed with 0.1 N NaOH and methylene chloride. The layers were separated and the aqueous layer was extracted with methylene chloride. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound as a solid. 1H NMR (400 MHz, d6-DMSO): 8.39 (br s, 1H), 8.08 (s, 1H) 7.25 (m, 4H), 4.00 (s, 2H), 3.48 (m, 2H), 2.84 (t, 2H), 2.41 (br s, 2H); MS (ESI-LCMS) for C13H14ClN3OS: 296 (MH+).

Workup

  1. customThe methanol and dioxane were removed in vacuo
  2. additionthe resulting solid was vigorously mixed with 0.1 N NaOH and methylene chloride
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with methylene chloride
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-960f3f09ecc04e3885bd0ac62fa7d3a4
Source dataset
uspto-grants-2011_07
Patent number
US07973061B2

Reaction notes

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