Triethylamine → HCID 131724908, compound

HRID 1272768Notes

Reaction equation

HRID 1272768 reaction equation
[NH2:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)NN=[C:8]2[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=[O:4].[CH2:21]([N:23](CC)CC)[CH3:22].Cl.[C:29](=N)(OCC)[CH3:30]>C(O)C>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:8]2[C:7]3[C:11](=[CH:12][CH:13]=[C:5]([C:3]([NH:2][NH:1][CH2:22][CH:21]=[NH:23])=[O:4])[CH:6]=3)[CH2:30][CH:29]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)2×HCID 22479863HCID 22479863, compound2×

Product 1

HCID 131724908HCID 131724908, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a flask containing N-amino[3-(4-fluorophenyl)(1H-indazol-5-yl)]carboxamide (196 mg, 0.73 mmol) under a nitrogen atmosphere was added anhydrous ethanol (3 mL) and triethylamine (0.1 mL, 0.73 mmol). In a separate flask ethyl acetimidate hydrochloride (90 mg, 0.73 mmol) was dissolved in anhydrous ethanol (2 mL) and triethylamine (0.1 mL, 0.73 mmol). The flask containing the N-amino[3-(4-fluorophenyl)(1H-indazole-5-yl)]carboxamide solution was placed on ice while the ethyl acetimidate hydrochloride solution was added dropwise to the chilled flask. The flask was kept at 0° C. for 2 hours and then allowed to stir at room temperature for two days. LC-MS indicated the reaction was complete. The solvent was removed and the compound was taken on crude into the next step of the synthesis. ES-MS m/z 312 [M+H]+.

Workup

  1. additionwas added dropwise to the chilled flask
  2. customThe solvent was removed
  3. customthe compound was taken on crude into the next step of the synthesis

Sources & evidence

ORD record
ord-695c721717354039981f34f1079e78dc
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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