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

HRID 623951

Reaction equation

HRID 623951 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 was stirred for 10 minutes and layers were separated. The CH2Cl2 layer was dried over Na2SO4 and filtered. The solvent was removed under reduced pressure and the residual oil was 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 was 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 was chromatographed (CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-88badfb1c2d54cc0a743e9f40cbe5eb1
Source dataset
uspto-grants-2016_04
Patent number
US09303015B2

Linked notes

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