Methyl chloroglyoxylate → HCID 178501789, compound

HRID 1394453Notes

Reaction equation

HRID 1394453 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:15]=[N:14][C:13]([C:16]2[NH:17][C:18]([CH3:21])=[N:19][N:20]=2)=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2.Cl[C:23]([C:25]([O:27][CH3:28])=[O:26])=[O:24]>C(Cl)Cl.C[N+]([O-])=O>[CH3:28][O:27][C:25](=[O:26])[C:23]([C:9]1[C:8]2[C:12](=[C:13]([C:16]3[NH:17][C:18]([CH3:21])=[N:19][N:20]=3)[N:14]=[CH:15][C:7]=2[O:6][CH3:5])[NH:11][CH:10]=1)=[O:24]

Participants

6

Reactant 3

HCID 79846Methyl chloroglyoxylateHCID 6451240Aluminum(III) ChlorideHCID 178493714HCID 178493714, compound

Product 1

HCID 178501789HCID 178501789, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6375NitromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of AlCl3 (0.321 g, 2.411 mmol) in CH2Cl2 (0.8 mL) and MeNO2 (0.2 mL) was added 4-methoxy-7-(5-methyl-1,3,4-triazol-2-yl)-6-azaindole (0.0435 g, 0.190 mmol) as a solid. After dissolution of the starting material (ca. 5 min), ClCOCO2Me (0.070 mL, 0.756 mmol) was added and the mixture was allowed to stir for 5 h. The mixture was then cooled at 0° C., quenched by the slow addition of 1 M aqueous NH4OAc and extracted with EtOAc (×3). The combined organic layers were washed (H2O, brine), dried (Na2SO4) and evaporated to give 4-methoxy-7-(5-methyl-1,3,4-triazol-2-yl)-6-azaindol-3-yl-oxoacetic acid methyl ester (0.0347 g, 60%: LCMS: m/e 316 (M+H)+. This material was dissolved in MeOH (2 mL) and treated with 2.5 M NaOH (0.2 mL, 0.5 mmol). The mixture was allowed to stir for 5 h, at which point the solvent was removed and the residue was diluted with H2O (2 mL). This mixture was acidified to pH 1 with 6 M HCl and the solution was lyophilized to give the title compound (0.062 g), which contained a nominal amount of inorganic salts. This material was used as such in the following step:

Workup

  1. additionwas added
  2. customquenched by the slow addition of 1 M aqueous NH4OAc
  3. extractionextracted with EtOAc (×3)
  4. washThe combined organic layers were washed (H2O, brine)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-79f09a9d956d4f52acd9d117d224eed1
Source dataset
uspto-grants-2008_03
Patent number
US07348337B2

Reaction notes

Loading…