Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86592992, compound

HRID 1296360Notes

Reaction equation

HRID 1296360 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([OH:15])=O)[N:10]=[C:9]2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:4][CH:3]=1.Cl.[CH3:25][NH:26][O:27][CH3:28].CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C1COCC1.C(OCC)(=O)C>[CH3:28][O:27][N:26]([CH3:25])[C:13]([C:11]1[N:10]=[C:9]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH:12]=1)=[O:15]

Participants

6

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 111923Propylphosphonic anhydrideHCID 11417294HCID 11417294, compound

Product 1

HCID 86592992HCID 86592992, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-1H-imidazole-4-carboxylic acid I-7d (1.31 g, 3.57 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.42 g, 1.2 equiv) in THF (14 ml) were added TEA (4.97 ml, 10 equiv) and 1-propane phosphonic acid cyclic anhydride (3.21 ml, 1.5 equiv). The reaction mixture was stirred at room temperature overnight, diluted with ethyl acetate and washed with water, 10% citric acid, and saturated aqueous sodium chloride. The organic phase was dried over anhydrous magnesium sulfate and concentrated to a foam which was purified by flash column chromatography (silica, 70:30 ethyl acetate/hexane grading to ethyl acetate) to give 1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-1H-imidazole-4-carboxylic acid methoxy-methyl-amide I-7e (485 mg, 33%).

Workup

  1. washwashed with water, 10% citric acid, and saturated aqueous sodium chloride
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated to a foam which
  4. customwas purified by flash column chromatography (silica, 70:30 ethyl acetate/hexane grading to ethyl acetate)

Sources & evidence

ORD record
ord-5897a58543874a9c912b95be7d6ff06b
Source dataset
uspto-grants-2007_07
Patent number
US07247628B2

Reaction notes

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