Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 54410660, compound

HRID 2300693Notes

Reaction equation

HRID 2300693 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[CH3:23])[O:11][C:12]=2[CH2:13][CH2:14][C:15](O)=[O:16])=[CH:4][CH:3]=1.Cl.[CH3:25][NH:26][O:27][CH3:28].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)(O)[O-].[Na+]>O.CN(C)C=O.C(N(CC)CC)C>[CH3:28][O:27][N:26]([CH3:25])[C:15](=[O:16])[CH2:14][CH2:13][C:12]1[O:11][C:10]([N:18]2[CH:22]=[CH:21][N:20]=[C:19]2[CH3:23])=[N:9][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

9

Reactant 5

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11034933HCID 11034933, compound

Product 1

HCID 54410660HCID 54410660, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Triethylamine(505 mg) was added dropwise to a N,N-dimethylformamide solution of 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionic acid(1.50 g) and N,O-dimethylhydroxyamine hydrochloride(490 mg) at 0° C. 1-Hydroxybenzotriazole hydrate(HOBt, 760 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride(WSC, 950 mg) were added thereto. The reaction mixture was stirred for 20 hours at room temperature. Water was poured into the reaction mixture. Saturated sodium bicarbonate solution was added to make the mixture alkaline. The resulting mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, and dried(MgSO4). The solvent was evaporated, and the precipitated crystals were collected by filtration to give N-methoxy-N-methyl-4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionamide(1.54 g, 91%). This was recrystallized from acetone-isopropyl ether to give colorless prisms. mp 116-117° C.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water, and dried(MgSO4)
  3. customThe solvent was evaporated
  4. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-9571c59dcbce48c785f3c08add4380f5
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

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