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Potassium Carbonate → 5-(2-Bromo-5-fluoro-pyridin-4-yl)-2,2-bis-fluoromethyl-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

HRID 538372
Notes
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Reaction equation

HRID 538372 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([NH:19]S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)([CH3:18])[CH2:9][O:10][C:11]([C:16]#[N:17])([CH2:14][F:15])[CH2:12][F:13])[C:5]([F:32])=[CH:4][N:3]=1.C(N[C@H](C(O)=O)CS)(=O)C.C([O-])([O-])=O.[K+].[K+]>CCO>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2([CH3:18])[CH2:9][O:10][C:11]([CH2:14][F:15])([CH2:12][F:13])[C:16]([NH2:17])=[N:19]2)[C:5]([F:32])=[CH:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 12035N-Acetyl-L-Cysteine2×HCID 86668082N-[1-(2-bromo-5-fluoro-pyridin-4-yl)-2-(cyano-bis-fluoromethyl-methoxy)-1-methyl-ethyl]-2-nitro-benzenesulfonamide

Product 1

HCID 866680815-(2-Bromo-5-fluoro-pyridin-4-yl)-2,2-bis-fluoromethyl-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Conditions

Temperature
85 °C

Procedure

A solution of N-[1-(2-bromo-5-fluoro-pyridin-4-yl)-2-(cyano-bis-fluoromethyl-methoxy)-1-methyl-ethyl]-2-nitro-benzenesulfonamide (840 mg, 1.563 mmol), N-acetyl-L-cysteine (510 mg, 3.13 mmol) and K2CO3 (432 mg, 3.130 mmol) in abs. EtOH (10 ml) was stirred at 85° C. for 18 h. N-acetyl-L-cysteine (250 mg, 1.533 mmol) and K2CO3 (210 mg, 1.519 mmol) was added and stirring at 85° C. was continued for 18 h. The reaction mixture was concentrated to ⅓ of its volume, quenched with 10% aq. K2CO3 soln. and 3× extracted with TBME. The combined org. phases were washed with sat. aq. NaHCO3 soln, brine, dried over Na2SO4, filtered and concentrated to leave the crude title compound that was purified by NP-HPLC (Alltech Grom Saphir65 Si 10 μm column, 150×30 mm, gradient n-heptane:EtOAc:MeOH 68:30:2 to 0:65:35),

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customquenched with 10% aq. K2CO3 soln
  3. extractionand 3× extracted with TBME
  4. washphases were washed with sat. aq. NaHCO3 soln
  5. dry with materialbrine, dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-223523e477914de296bfbee6393db119
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08865712B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes