Ethyl 2-chloro-5-{[(1-methyl-1-phenylethyl)amino]carbonyl}-1,3-thiazole-4-carboxylate → Ethyl 5-(aminocarbonyl)-2-chloro-1,3-thiazole-4-carboxylate

HRID 1948359Notes

Reaction equation

HRID 1948359 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:12]([NH:14]C(C)(C2C=CC=CC=2)C)=[O:13])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1>C(O)(C(F)(F)F)=O>[NH2:14][C:12]([C:4]1[S:3][C:2]([Cl:1])=[N:6][C:5]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:13]

Participants

3

Reactant 1

HCID 68519289Ethyl 2-chloro-5-{[(1-methyl-1-phenylethyl)amino]carbonyl}-1,3-thiazole-4-carboxylate2×

Product 1

HCID 59406883Ethyl 5-(aminocarbonyl)-2-chloro-1,3-thiazole-4-carboxylateYield 40.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 210 mg of ethyl 2-chloro-5-{[(1-methyl-1-phenylethyl)amino]carbonyl}-1,3-thiazole-4-carboxylate (Intermediate 233) in 5 ml TFA was stirred at room temperature overnight. Solvent was removed and the residue was dissolved in 5 ml MeOH. Solvent was again removed and the residue was triturated with ether to give 57 mg of a white solid. NMR (d6-DMSO): 1.3 (t, 3H), 4.3 (q, 2H), 8.2 (s, 1H), 8.8 (s, 1H).

Workup

  1. customSolvent was removed
  2. dissolutionthe residue was dissolved in 5 ml MeOH
  3. customSolvent was again removed
  4. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-a8c869e805664c9a8ad3ccebcad7f078
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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