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

HRID 45838Notes

Reaction equation

HRID 45838 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]=C(C4C=CC=CC=4)C4C=CC=CC=4)[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].Cl.C(OCC)C>O1CCOCC1>[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86654336N-tert-butyl-4-[3-{3-[(diphenylmethylidene)amino]phenyl}-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridin-2-amine

Product 1

HCID 671840184-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-N-tert-butyl-pyridin-2-amineYield 46.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

120 mg (0.2 mmol) of N-tert-butyl-4-[3-{3-[(diphenylmethylidene)amino]phenyl}-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridin-2-amine were dissolved in 20 ml of 1,4-dioxane and 5 ml of HCl 4M in dioxane were added. After 4 hours the solvent was removed in vacuo and the residue dissolved in dichloromethane and washed with aqueous NaHCO3. The organic layer was dried over Na2SO4 and evaporated to give, after trituration with diethylether, 40 mg (46% yield) of the title compound.

Workup

  1. customAfter 4 hours the solvent was removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with aqueous NaHCO3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated
  6. customto give

Sources & evidence

ORD record
ord-2ef14dda9f924c7ebc2f49c249a3d449
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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