Triethylamine → HCID 178440322, compound

HRID 2183130Notes

Reaction equation

Cl.C(O[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[NH:6])C.C([N:25](CC)CC)C.[C:30]([NH:35]N)(=O)[CH:31]([CH3:33])[CH3:32]>C(O)C>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[C:7]([C:5]4[NH:25][C:30]([CH:31]([CH3:33])[CH3:32])=[N:35][N:6]=4)[CH:8]=3)[NH:12][N:11]=2)=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a flask containing ethoxy[3-(4-fluorophenyl)(1H-indazole-5-yl)]methanimine hydrochloride (106 mg, 0.37 mmol) was added absolute ethanol (2.5 mL) and triethylamine (0.15 mL, 1.11 mmol). The flask was placed on ice and to the flask was added a solution of isobutyric acid hydrazide (37.7 mg, 0.37 mmol) in absolute ethanol was heated at 60° C. for fifteen hours. An additional two equivalents of the isobutyric acid hydrazide (75 mg, 0.74 mmol) and triethylamine (0.2 mL, 1.35 mmol) was added to the reaction and allowed to stir overnight. Reaction was continuing to progress slowly, two equivalents of the isobutyric acid hydrazide (75 mg, 0.74 mmol) and triethylamine (0.2 ml, 1.35 mmol) were added to the reaction and allowed to stir overnight. The reaction was stopped. Solvent was removed by rotary evaporation and the product was purified by HPLC to yield the title compound (53 mg, 45% yield). 1H NMR (DMSO-d6) δ 13.5 (s, 1H), 8.6 (s,1H), 8.0-8.1 (m, 3H), 7.7 (m, 1H), 7.35-7.5 (m, 2H), 1.4 (m, 7H), ES-MS (m/z) 322 [M+1]+.

Workup

customReaction
stirringto stir overnight
customSolvent was removed by rotary evaporation
customthe product was purified by HPLC

Sources & evidence

ORD record: ord-da752bac57644c4ebe22c80d276292df
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06897231B2

Reaction notes

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