Diisopropylethylamine → N-(2-(4-fluorophenyl)-2-methylpropyl)-6-(1H-pyrazol-1-yl)pyridazin-3-amine

HRID 869138Notes

Reaction equation

Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)=[CH:6][CH:7]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:24])([CH3:23])[CH2:21][NH2:22])=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C>CN1C(=O)CCC1>[F:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]([CH3:24])([CH3:23])[CH2:21][NH:22][C:2]2[N:3]=[N:4][C:5]([N:8]3[CH:12]=[CH:11][CH:10]=[N:9]3)=[CH:6][CH:7]=2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 250 °C

Procedure

To a 5 mL microwave vial was added 3-chloro-6-(1H-pyrazol-1-yl)pyridazine (320 mg, 1.8 mmol, 1.0 equiv), 2-(4-fluorophenyl)-2-methylpropan-1-amine (386 mg, 2.3 mmol, 1.3 equiv), diisopropylethylamine (620 μL, 3.6 mmol, 2.0 equiv), and NMP (4 mL). The reaction was heated in a microwave reactor to 250° C. and stirred for 15 min. A portion (roughly a third) of the reaction was purified by reverse phase chromatography and then silica gel chromatography (10% MeOH/DCM) to give 61 mg of N-(2-(4-fluorophenyl)-2-methylpropyl)-6-(1H-pyrazol-1-yl)pyridazin-3-amine, m/z=312.1 [M+H].

Workup

customA portion (roughly a third) of the reaction was purified by reverse phase chromatography

Sources & evidence

ORD record: ord-34713004e04a476c87af277e3ce9375c
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969346B2

Reaction notes

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