Hydrochloric Acid → HCID 57667988, compound

HRID 2191844Notes

Reaction equation

HRID 2191844 reaction equation
I[C:2]1[CH:10]=[C:9]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[CH:23]2.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+].Cl>[Cu]I.C(OCC)(=O)C.CS(C)=O>[NH:25]1[C:26]2[C:22](=[CH:21][C:20]([NH:19][C:2]3[CH:10]=[C:9]([CH2:11][CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:8]=[CH:7][C:3]=3[C:4]([OH:6])=[O:5])=[CH:28][CH:27]=2)[CH:23]=[N:24]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 880121H-Indazol-5-amineHCID 145742L-ProlineHCID 57667811HCID 57667811, compound

Product 1

HCID 57667988HCID 57667988, compoundYield 9.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To 2-iodo-4-phenethylbenzoic acid 40 mg were added 5-aminoindazole 23 mg, copper(I) iodide 2.2 mg, proline 2.6 mg, potassium carbonate 19 mg and dimethyl sulfoxide 0.40 mL at room temperature, and it was stirred at 70° C. for 3 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 1.0 mol/L hydrochloric acid were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with water and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; chloroform:methanol=100:1] to give 2-((1H-indazol-5-yl)amino)-4-phenethylbenzoic acid 4.0 mg of a white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washafter sequential washing with water and saturated sodium chloride aqueous solution
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-415b726df2524fe39db409bbfc11afbc
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

Loading…