Water → 4-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-N-tert-butyl-pyridin-2-amine

HRID 45858Notes

Reaction equation

[C:1]([NH:5][C:6]1[CH:11]=[C:10]([C:12]2[C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-])=O)[CH:27]=3)=[N:14][N:15]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH:16]=2)[CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].O.[Cl-].[NH4+]>O1CCOCC1.[Zn]>[NH2:32][C:28]1[CH:27]=[C:26]([C:13]2[C:12]([C:10]3[CH:9]=[CH:8][N:7]=[C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:11]=3)=[CH:16][N:15]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=3)[N:14]=2)[CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 100 °C

Procedure

400 mg (0.87 mmol) of N-tert-butyl-4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyridin-2-amine were dissolved in 15 ml of dioxane and 4 ml of water and 227 mg (3.48 mmol) of metallic zinc and 461 (8.7 mmol) of ammonium chloride were added. The mixture was stirred at 100° C. for 4 hours, then filtered through a celite pad. The filtrate was evaporated and the residue partitioned between dichloromethane and aqueous sodium hydrogenocarbonate. The organic phase was then dried and evaporated and the residue purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3 from 9/1 to 7/3), giving 180 mg (48%) of the title compound.

Workup

filtrationfiltered through a celite pad
customThe filtrate was evaporated
customthe residue partitioned between dichloromethane and aqueous sodium hydrogenocarbonate
customThe organic phase was then dried
customevaporated
customthe residue purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3 from 9/1 to 7/3)

Sources & evidence

ORD record: ord-85d9ef4c80714ab686815ae47761bf76
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541575B2

Reaction notes

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