Diethyl Ether → 4-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-N-methylpyridin-2-amine

HRID 45865Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[CH:14]=3)[C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-])=O)[CH:22]=3)=[N:9]2)=[CH:5][CH:4]=1.[Cl-].[NH4+].C(OCC)C>O1CCOCC1.O.[Zn]>[NH2:27][C:23]1[CH:22]=[C:21]([C:10]2[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[CH:14]=3)=[CH:12][N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:31][CH:30]=3)[N:9]=2)[CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

300 mg (0.72 mmol) of 4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]-N-methylpyridin-2-amine were dissolved in a mixture of 20 ml of dioxane and 4 ml of water and 381 mg (7.2 mmol) of ammonium chloride and 190 mg (2.9 mmol) of metallic zinc were added. The reaction was maintained at 100° C. under stirring for 6 hours. The mixture was then filtered through a celite pad and the solvent removed in vacuo. The residue was partitioned between dichloromethane and water, dried over sodium sulphate and evaporated again, giving, after trituration with diethylether, 260 mg (93%) of the title compound.

Workup

additionwere added
filtrationThe mixture was then filtered through a celite pad
customthe solvent removed in vacuo
customThe residue was partitioned between dichloromethane and water
dry with materialdried over sodium sulphate
customevaporated again
customgiving

Sources & evidence

ORD record: ord-7e1c7f48e2e34e4ba4d2a64ae92af172
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541575B2

Reaction notes

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