Chloroform → 4-{3-Isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(piperidin-4-ylamino)benzonitrile

HRID 1625233Notes

Reaction equation

HRID 1625233 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3=[N:14][CH:15]=[CH:16][C:17]([C:18]4[CH:19]=[N:20][C:21]5[C:26]([CH:27]=4)=[CH:25][CH:24]=[CH:23][CH:22]=5)=[C:12]3[C:11]([CH:28]([CH3:30])[CH3:29])=[N:10]2)=[CH:5][C:4]=1[NH:31][CH:32]1[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]1)#[N:2].C(Cl)(Cl)Cl.O.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[CH:28]([C:11]1[C:12]2[C:13](=[N:14][CH:15]=[CH:16][C:17]=2[C:18]2[CH:19]=[N:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([NH:31][CH:32]3[CH2:33][CH2:34][NH:35][CH2:36][CH2:37]3)[CH:5]=2)[N:10]=1)([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 67501198Tert-butyl 4-{2-cyano-5-(3-isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl)phenylamino}piperidine-1-carboxylateHCID 86585896Sodium bicarbonate water

Product 1

HCID 675014474-{3-Isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(piperidin-4-ylamino)benzonitrileYield 56%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl 4-{2-cyano-5-(3-isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl)phenylamino}piperidine-1-carboxylate obtained in Example 76 was dissolved in trifluoroacetic acid, followed by stirring at room temperature for 1 hr. The reaction solution was distributed between chloroform and saturated sodium bicarbonate water, and the organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate. After distillation of the solvent, the residue was purified by neutral silica gel column chromatography (chloroform/methanol) to obtain (77a) (the second stage yield: 56%) as a white solid.

Workup

  1. washthe organic layer was washed with saturated saline
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationAfter distillation of the solvent
  4. customthe residue was purified by neutral silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-67de03c0d4704f439ed561b354168c7f
Source dataset
uspto-grants-2014_07
Patent number
US08779142B2

Reaction notes

Loading…