Hydrazine hydrate (1:1) → Ethanamine, 2-[(4-chlorophenyl)[4-(1H-pyrazol-4-yl)phenyl]methoxy]-

HRID 45525Notes

Reaction equation

O.NN.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:34]=[N:35][NH:36][CH:37]=3)=[CH:29][CH:28]=2)[O:12][CH2:13][CH2:14][NH:15]C(=O)C2C(=CC=CC=2)C(O)=O)=[CH:7][CH:6]=1>CO>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:37]=[N:36][NH:35][CH:34]=3)=[CH:29][CH:28]=2)[O:12][CH2:13][CH2:14][NH2:15])=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Hydrazine monohydrate (159 □l, 3.28 mmol) was added to a solution of N-(2-{(4-Chloro-phenyl)-[4-(1H-pyrazol-4-yl)-phenyl]-methoxy}-ethyl)-phthalamic acid (260 mg, 0.55 mmol) in methanol (6 ml) and the reaction mixture stirred at 80° C. for 16 hours. Upon cooling, the solvent was removed under reduced pressure and the crude product was purified by column chromatography (SiO2), eluting with dichloromethane:methanol:acetic acid:water (90:18:3:2). Further purification by Phenomenex_Strata_SCX column chromatography, eluting with methanol followed by 2N ammonia in methanol, afforded the desired product as the free base (120 mg). LC/MS: (FL-A) Rt 2.07 [M-NH2CH2CH2O+H]+ 267. 1H NMR (Me-d3-OD) δ 2.85 (2H, t), 3.55 (2H, t), 5.45 (1H, s), 7.35-7.40 (6H, m), 7.58 (2H, d), 7.95 (2H, s).

Workup

temperatureUpon cooling
customthe solvent was removed under reduced pressure
customthe crude product was purified by column chromatography (SiO2)
washeluting with dichloromethane:methanol:acetic acid:water (90:18:3:2)
customFurther purification by Phenomenex_Strata_SCX column chromatography
washeluting with methanol

Sources & evidence

ORD record: ord-3feb823cb36b4d58906cf8044a6da360
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541461B2

Reaction notes

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