Triethylamine → N-methoxy-N,1-dimethyl-1H-imidazole-5-carboxamide

HRID 928777Notes

Reaction equation

HRID 928777 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]1[C:13]([C:14]([OH:16])=O)=[CH:12][N:11]=[CH:10]1.Cl.[CH3:18][NH:19][O:20][CH3:21].CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:21][O:20][N:19]([CH3:18])[C:14]([C:13]1[N:9]([CH3:8])[CH:10]=[N:11][CH:12]=1)=[O:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27735071-methyl-1H-imidazole-5-carboxylic acid

Product 1

HCID 59677368N-methoxy-N,1-dimethyl-1H-imidazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (5.51 mL, 39.646 mmol) was added slowly to a mixture of commercially available 1-methyl-1H-imidazole-5-carboxylic acid (2 g, 15.859 mmol), N,O-dimethylhydroxylamine hydrochloride (1.55 g, 15.859 mmol), and EDCI (3.65 g, 19.03 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, then filtered. The solvent was removed under reduced pressure and the residual oil chromatographed (CH2Cl2/EtOAc) to provide the product as a 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 chromatographed (CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-3b9a8f80763c46a89dbb1ded1b6685ba
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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