HCID 89500351, compound → HCID 71549815, compound

HRID 925459Notes

Reaction equation

HRID 925459 reaction equation
C(OC(=O)[NH:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:16]2[CH:21]=[C:20]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][C:25]=3[Cl:31])[CH:19]=[CH:18][C:17]=2[F:32])([CH2:14][F:15])[N:13]=1)(C)(C)C>Cl.O1CCOCC1.Cl.CO>[Br:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][NH:22][C:20]2[CH:19]=[CH:18][C:17]([F:32])=[C:16]([C:12]3([CH2:14][F:15])[CH2:11][O:10][CH2:9][C:8]([NH2:7])=[N:13]3)[CH:21]=2)=[C:25]([Cl:31])[CH:26]=1

Participants

4

Reactant 1

HCID 89500351HCID 89500351, compound

Product 1

HCID 71549815HCID 71549815, compound

Reagents, catalysts & solvents 2

HCID 21893726Hydrochloride methanolCatalystHCID 204431481,4-Dioxane hydrochlorideSolvent

Conditions

Temperature
50 °C

Procedure

{5-[5-(4-Bromo-2-chloro-benzylamino)-2-fluoro-phenyl]-5-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl}-carbamic acid tert-butyl ester (82 mg, 0.151 mmol) were suspended in 1.1 ml HCl/Dioxane (4M). A few drops HCl/MeOH (3M) were added and the mixture was stirred at 50° C. for 2 h. The mixture was evaporated, taken up in 10% aq soda, extracted with DCM and dried with Na2SO4. The title compound was purified via chromatography on silica gel [DCM/1-5%(MeOH/DCM 10:90)]. The product was dissolved in Et2O and precipitated as its hydrochloride salt by adding 1N HCl/Et2O.

Workup

  1. customThe mixture was evaporated
  2. extractionextracted with DCM
  3. dry with materialdried with Na2SO4
  4. customThe title compound was purified via chromatography on silica gel [DCM/1-5%(MeOH/DCM 10:90)]
  5. dissolutionThe product was dissolved in Et2O
  6. customprecipitated as its hydrochloride salt
  7. additionby adding 1N HCl/Et2O

Sources & evidence

ORD record
ord-589f0d7b0e094e80807f2f499a800718
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

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