Triethylamine → N-Methoxy-N-methyl-1,3-thiazole-5-carboxamide

HRID 928735

Reaction equation

HRID 928735 reaction equation
C(N(CC)CC)C.[S:8]1[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[CH:9]1.Cl.[CH3:17][NH:18][O:19][CH3:20].CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:20][O:19][N:18]([CH3:17])[C:13]([C:12]1[S:8][CH:9]=[N:10][CH:11]=1)=[O:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 84494Thiazole-5-carboxylic acid

Product 1

HCID 25307138N-Methoxy-N-methyl-1,3-thiazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.77 mL, 19.9 mmol) was added slowly to a mixture of commercially available thiazole-5-carboxylic acid (1.03 g, 7.98 mmol), N,O-dimethylhydroxylamine hydrochloride (0.778 g, 7.98 mmol), and EDCI (1.83 g, 9.57 mmol) in CH2Cl2 (10 mL). The mixture was stirred at room temperature for 72 hours then quenched with saturated aqueous NaHCO3. Water (50 mL) was added followed by additional CH2Cl2. The mixture as stirred for 10 minutes and layers were separated. The CH2Cl2 layer was dried over Na2SO4, then filtered. The solvent was removed under reduced pressure and the residual oil chromatographed (CH2Cl2/EtOAc) to provide the title compound as a white solid.

Workup

  1. customthen quenched with saturated aqueous NaHCO3
  2. additionWater (50 mL) was added
  3. stirringThe mixture as stirred for 10 minutes
  4. customlayers were separated
  5. dry with materialThe CH2Cl2 layer was dried over Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customthe residual oil chromatographed (CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-de14795b9123410b8e52f0cf96fc86ae
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Linked notes

Loading…