Hydrochloric Acid → 3-(1-(2,3-difluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl)pyridin-2-amine

HRID 253974Notes

Reaction equation

C([NH:5][C:6]1[C:11]([C:12]2[N:13]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=3[F:28])[C:14]3[CH:19]=[CH:18][N:17]=[CH:16][C:15]=3[N:20]=2)=[CH:10][CH:9]=[CH:8][N:7]=1)(C)(C)C.Cl.[OH-].[Na+]>CO>[F:28][C:22]1[C:23]([F:27])=[CH:24][CH:25]=[CH:26][C:21]=1[N:13]1[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[N:20]=[C:12]1[C:11]1[C:6]([NH2:5])=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of N-tert-butyl-3-(1-(2,3-difluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl)pyridin-2-amine (1.5 g, 3.95 mmol) in methanol (7.0 mL) was added 6N aq. HCl at room temperature and the mixture heated at reflux for 5 hr. After cooling to 0° C., the pH of the solution was adjusted to pH 8-9 with 2N aq. NaOH solution (150 mL). The resulting precipitate was filtered off and dissolved in EtOAc (300 mL). The combined organics were washed with water (3×100 mL), brine (100 mL), and dried (Na2SO4). Filtration and evaporation of solvent in vacuo gave a solid, which was triturated with petroleum ether (3×20 mL) to give 3-(1-(2,3-difluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl)pyridin-2-amine (0.9 g, 75% yield) as a light yellow solid; LC-MS: 324.0 (M+H).

Workup

temperaturethe mixture heated
temperatureat reflux for 5 hr
filtrationThe resulting precipitate was filtered off
dissolutiondissolved in EtOAc (300 mL)
washThe combined organics were washed with water (3×100 mL), brine (100 mL)
dry with materialdried (Na2SO4)
filtrationFiltration and evaporation of solvent in vacuo
customgave a solid, which
customwas triturated with petroleum ether (3×20 mL)

Sources & evidence

ORD record: ord-996bae7c07994375b00894bb9ed7a72a
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872031B2

Reaction notes

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