Methanol → HCID 20730321, compound

HRID 352157Notes

Reaction equation

HRID 352157 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]([C:18]3[NH:22][C:21]([C:23]([OH:25])=[O:24])=[CH:20][N:19]=3)=[O:17])=[CH:8]2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:33]O>C(OCC)(=O)C.CCCCCC>[CH3:33][O:24][C:23]([C:21]1[NH:22][C:18]([C:16]([C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:7]([CH2:6][C:5]3[CH:26]=[CH:27][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:8]=2)=[O:17])=[N:19][CH:20]=1)=[O:25]

Participants

6

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22022401HCID 22022401, compound

Product 1

HCID 20730321HCID 20730321, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-[1-(4-chloro-benzyl)-1H-indole-3-carbonyl]-3H-imidazole-4-carboxylic acid (60 mg) and concentrated sulfuric acid (1 mL) in methanol (100 mL) was heated to reflux overnight. After removal of solvent, the mixture was dissolved in ethyl acetate and washed with 5% sodium hydroxide solution. The organic layers were dried over magnesium sulfate and evaporated to dryness. The product 2-[1-(4-chloro-benzyl)-1H-indole-3-carbonyl]-3H-imidazole-4-carboxylic acid methyl ester (55 mg, yield 89%) was purified by flash column chromatography (ethyl acetate:hexane=1:1). 1H NMR (acetone-d6) δ3.84 (s, 3H), 5.65 (s, 2H), 7.2-7.4 (m, 6H), 7.48 (m, 1H), 7.95 (s, 1H), 8.45 (m, 1H), 9.48(s, 1H) ppm; ESMS calcd (C21H16ClN3O3): 393.09; found: 394.1 (M+H)+.

Workup

  1. temperatureto reflux overnight
  2. customAfter removal of solvent
  3. dissolutionthe mixture was dissolved in ethyl acetate
  4. washwashed with 5% sodium hydroxide solution
  5. dry with materialThe organic layers were dried over magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-812c5320cab74fe198a07ffe613b1578
Source dataset
uspto-grants-2004_06
Patent number
US06743919B2

Reaction notes

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