Trifluoroacetic acid → HCID 71549814, compound

HRID 925450Notes

Reaction equation

HRID 925450 reaction equation
C(OC(=O)[NH:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:15]2[CH:20]=[C:19]([NH:21][CH2:22][C:23]3[O:24][CH:25]=[CH:26][CH:27]=3)[CH:18]=[CH:17][C:16]=2[F:28])([CH3:14])[N:13]=1)(C)(C)C.Cl.O1CCOCC1.C(O)(C(F)(F)F)=O>>[F:28][C:16]1[CH:17]=[CH:18][C:19]([NH:21][CH2:22][C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)=[CH:20][C:15]=1[C:12]1([CH3:14])[CH2:11][O:10][CH2:9][C:8]([NH2:7])=[N:13]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 204431481,4-Dioxane hydrochlorideHCID 89500527HCID 89500527, compound

Product 1

HCID 71549814HCID 71549814, compound

Conditions

Temperature
50 °C

Procedure

A solution of (5-{2-fluoro-5-[(furan-2-ylmethyl)-amino]-phenyl}-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl)-carbamic acid tert-butyl ester (29 mg, 0.072 mmol) in 4M HCl/dioxane (0.719 ml, 2.88 mmol) was stirred at rt for 2 h, then heated at 50° C. for 2 h. TFA (0.005 ml, 0.072 mmol) was added and stirring at 50° C. was continued for 7 h. The reaction mixture was quenched with water and diluted with EtOAc. The phases were separated and the aq. layer was twice reextracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to leave the crude title compound that was purified by RP-HPLC (Waters SunFire C18 column, 5 μM, 19×150 mm, gradient 10 to 90% ACN+0.1% TFA) and obtained as a free base after filtration over an SCX cartridge.

Workup

  1. customThe reaction mixture was quenched with water
  2. additiondiluted with EtOAc
  3. customThe phases were separated
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6b68335dcc684287b129cf7df0d03311
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

Loading…