Hydrazine → 4-(5-(4-Chlorophenyl)-6-hydrazinyl-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-oxo-2,3-dihydropyridazin-4-yl)benzonitrile

HRID 1865835Notes

Reaction equation

Br[C:2]1[C:3]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[C:4]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[C:5](=[O:20])[N:6]([CH2:8][C:9]2[C:10]([CH3:19])=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=2)[N:7]=1.[NH2:36][NH2:37]>N1C=CC=CC=1>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([C:3]2[C:2]([NH:36][NH2:37])=[N:7][N:6]([CH2:8][C:9]3[C:10]([CH3:19])=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=3)[C:5](=[O:20])[C:4]=2[C:21]2[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=2)=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 200 °C

Procedure

To a microwave flask was added 4-(6-bromo-5-(4-chlorophenyl)-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-oxo-2,3-dihydropyridazin-4-yl)benzonitrile (105 mg, 0.187 mmol), pyridine (10 ml) and anhydrous hydrazine (60 mg, 1.87 mmol). The reaction was subjected to microwaves with heating to 200° C. and the conditions were continued at that temperature for 1.5 hr. After this time, the reaction was cooled to rt and the solvent was removed to give product as yellow solid. The product was used in the next reaction without further purification.

Workup

temperatureAfter this time, the reaction was cooled to rt
customthe solvent was removed
customto give product as yellow solid
customThe product was used in the next reaction without further purification

Sources & evidence

ORD record: ord-adef22c1825447c4bae5d5edc0a543c4
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629342B2

Reaction notes

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