Hydrochloric Acid → HCID 68325528, compound

HRID 2403276Notes

Reaction equation

HRID 2403276 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=3)=[CH:16][CH:15]=2)[CH2:9]1)=O)(C)(C)C.Cl.[OH-].[Na+]>C1COCC1.O1CCOCC1>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:17]2[CH:16]=[CH:15][C:14]([CH:10]3[O:11][CH2:12][CH2:13][NH:8][CH2:9]3)=[CH:19][CH:18]=2)=[N:22][CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68325410HCID 68325410, compound

Product 1

HCID 68325528HCID 68325528, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of (RS)-2-[4-(5-chloro-pyridin-2-ylamino)-phenyl]-morpholine-4-carboxylic acid tert-butyl ester (50 mg) in THF (2 ml) was added dropwise a solution of hydrogen chloride in dioxane (0.26 ml, 4 M solution) and the mixture was heated at 60° C. overnight. The mixture was then cooled to room temperature and poured into 1 M aq. sodium hydroxide solution. The mixture was extracted twice with ethyl acetate and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (Isolute® Flash-NH2 from Separtis; gradient: heptane/ethyl acetate/methanol) to afford (RS)-(5-chloro-pyridin-2-yl)-(4-morpholin-2-yl-phenyl)-amine (19 mg, 51%) as a white solid. MS (ISP): 292.1 ([{37Cl}M+H]+), 290.1 ([{35Cl}M+H]+).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (Isolute® Flash-NH2 from Separtis; gradient: heptane/ethyl acetate/methanol)

Sources & evidence

ORD record
ord-09a6e31e20604821aafa0e0f706c1ea9
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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