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 1852940Notes

Reaction equation

HRID 1852940 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-519ac2b2beaa4e0e935590dd73a1f93e
Source dataset
uspto-grants-2015_02
Patent number
US08962619B2

Reaction notes

Loading…