Triethylamine → Methyl 4-amino-2-(2-methylmorpholino)thiazole-5-carboxylate

HRID 1958016Notes

Reaction equation

HRID 1958016 reaction equation
[C:1]([N:3]=[C:4]([N:7]1[CH2:12][CH2:11][O:10][CH:9]([CH3:13])[CH2:8]1)[S:5][CH3:6])#[N:2].SC[C:16]([O:18][CH3:19])=[O:17].C(N(CC)CC)C>CO>[NH2:2][C:1]1[N:3]=[C:4]([N:7]2[CH2:12][CH2:11][O:10][CH:9]([CH3:13])[CH2:8]2)[S:5][C:6]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 80489835Methyl N-cyano-2-methylmorpholine-4-carbimidothioate

Product 1

HCID 66780183Methyl 4-amino-2-(2-methylmorpholino)thiazole-5-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl N-cyano-2-methylmorpholine-4-carbimidothioate (1.2 g, 6 mmol), methyl 2-mercaptoacetate (0.64 g, 6 mmol) and triethylamine (1.2 g, 12.0 mmol) in methanol (50 mL) was stirred at ambient temperature overnight. Solvent was removed. The residue was dissolved in dichloromethane, washed with water and brine. The organic layer was concentrated to give the desired product (crude, 1.4 g, 93%). 1H NMR (300 MHz, CDCl3) δ 5.81 (br, 2H), 3.97˜3.94 (m, 1H), 3.75 (s, 3H), 3.69-3.59 (m, 3H), 3.28-3.14 (m, 1H), 2.87-2.80 (m, 1H), 1.22 (d, J=6.0 Hz, 3H); LC-MS: 258 (MH+).

Workup

  1. customSolvent was removed
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with water and brine
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-2e5d5c23ab1b468680fa691727ec48ff
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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