Triethylamine → HCID 178486823, compound

HRID 34054Notes

Reaction equation

HRID 34054 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:21]([NH:23][NH2:24])=O)[C:17]=3[O:19][CH3:20])[NH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[C:26](=[NH:30])(OC)[CH3:27].C(N(CC)CC)C>C(O)C>[F:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:21]4[NH:23][N:24]=[C:26]([CH3:27])[N:30]=4)[C:17]=3[O:19][CH3:20])[NH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)HCID 59797334HCID 59797334, compound

Product 1

HCID 178486823HCID 178486823, compoundYield 5.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of 19 mg of 3-[(E)-2-(3-fluorophenyl)-vinyl]-4-methoxy-1H-indazole-5-carboxylic acid hydrazide in 4 mL of ethanol were added 50 mg of O-methyl acetimidate hydrochloride and 0.19 mL of triethylamine, and stirred in a sealed tube at 150° C. for 17.5 hours. The reaction solution was allowed to cool to room temperature, the solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography, and further purified and separated by LC-MS, to afford 1.17 mg of the title compound as a yellow amorphous.

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent was evaporated
  3. customthe crude product was purified
  4. customseparated by silica gel column chromatography
  5. customfurther purified
  6. customseparated by LC-MS

Sources & evidence

ORD record
ord-cdbf15a6045f42479155e58f3cf0057d
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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