1,4-Dioxane hydrochloride → 2-[(3-{3-[4-(1-Aminocyclobutyl)phenyl]-2-(2-aminopyridin-3-yl)-3H-imidazo[4,5-b]pyridin-5-yl}phenyl)amino]ethanol trihydrochloride

HRID 1914049Notes

Reaction equation

HRID 1914049 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[N:26]([C:27]3[CH:32]=[CH:31][C:30]([C:33]4([NH:37]C(=O)OC(C)(C)C)[CH2:36][CH2:35][CH2:34]4)=[CH:29][CH:28]=3)[C:11]3=[N:12][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][CH2:23][CH2:24][OH:25])[CH:17]=4)=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[ClH:45].O1CCOCC1>C(Cl)Cl>[ClH:45].[ClH:45].[ClH:45].[NH2:37][C:33]1([C:30]2[CH:31]=[CH:32][C:27]([N:26]3[C:11]4=[N:12][C:13]([C:16]5[CH:17]=[C:18]([NH:22][CH2:23][CH2:24][OH:25])[CH:19]=[CH:20][CH:21]=5)=[CH:14][CH:15]=[C:10]4[N:9]=[C:8]3[C:7]3[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][CH:6]=3)=[CH:28][CH:29]=2)[CH2:34][CH2:35][CH2:36]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 71142528tert-Butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-{3-[(2-hydroxyethyl)amino]phenyl}-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate

Product 1

HCID 866753582-[(3-{3-[4-(1-Aminocyclobutyl)phenyl]-2-(2-aminopyridin-3-yl)-3H-imidazo[4,5-b]pyridin-5-yl}phenyl)amino]ethanol trihydrochlorideYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-{3-[(2-hydroxyethyl)amino]phenyl}-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate (73.0 mg, 0.123 mmol) was dissolved in DCM (1 mL). 4M HCl/dioxane (1 mL) was added to the minute and stirred at room temperature for 3.5 hours. The mixture was concentrated and solidified with ether. The precipitated solids were collected by filtration and washed with ether to afford desired product (61.2 mg, 82.6%) as yellow solid.

Workup

  1. concentrationThe mixture was concentrated
  2. filtrationThe precipitated solids were collected by filtration
  3. washwashed with ether

Sources & evidence

ORD record
ord-9cb0deeaf7804a3cb25154975e3bad5a
Source dataset
uspto-grants-2013_12
Patent number
US08609688B2

Reaction notes

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