(2-Methoxyethyl)hydrazine → 2-Acetylamino-5-[2-(2-methoxy-ethyl)-2H-pyrazol-3-yl]-4-trifluoromethyl-benzoic acid methyl ester

HRID 906582Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([C:10](=O)/[CH:11]=[CH:12]/N(C)C)[C:7]([C:17]([F:20])([F:19])[F:18])=[CH:6][C:5]=1[NH:21][C:22](=[O:24])[CH3:23].[CH3:26][O:27][CH2:28][CH2:29][NH:30][NH2:31]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([C:10]2[N:30]([CH2:29][CH2:28][O:27][CH3:26])[N:31]=[CH:12][CH:11]=2)[C:7]([C:17]([F:18])([F:20])[F:19])=[CH:6][C:5]=1[NH:21][C:22](=[O:24])[CH3:23]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-acetylamino-5-((E)-3-dimethylamino-acryloyl)-4-trifluoromethyl-benzoic acid methyl ester (600 mg, 1.67 mmol) and (2-methoxy-ethyl)-hydrazine (151 mg, 1.68 mmol) in toluene (10 mL) was stirred at 90° C. for 40 h. Four portions of (2-methoxy-ethyl)-hydrazine (one equiv each day) were added over 4 d and the mixture was kept at 90° C. The mixture was concentrated to dryness in vacuo. The crude product was purified by flash chromatography (silica gel, DCM/MeOH (100:0 to 60:40)) to provide the title compound as a yellow syrup (352 mg, 55%). ES-MS: m/z 386.3 [M+H]+, rt 5.50 min.

Workup

customwas kept at 90° C
concentrationThe mixture was concentrated to dryness in vacuo
customThe crude product was purified by flash chromatography (silica gel, DCM/MeOH (100:0 to 60:40))

Sources & evidence

ORD record: ord-307e0c7c99134416ab3244fd775de18a
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012988B2

Reaction notes

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