Triethylamine → HCID 118092731, compound

HRID 2207400Notes

Reaction equation

HRID 2207400 reaction equation
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.[CH3:47][C:48]1[CH:49]=[C:50]([C:65]2[CH:66]=[CH:67][C:68]([C:71](O)=[O:72])=[N:69][CH:70]=2)[CH:51]=[C:52]([NH:54][C:55]2[N:60]=[C:59]([C:61]([F:64])([F:63])[F:62])[CH:58]=[CH:57][N:56]=2)[CH:53]=1>O.CN(C=O)C>[CH3:47][C:48]1[CH:49]=[C:50]([C:65]2[CH:66]=[CH:67][C:68]([C:71]([N:3]3[CH2:4][CH2:5][O:1][C:2]3=[O:6])=[O:72])=[N:69][CH:70]=2)[CH:51]=[C:52]([NH:54][C:55]2[N:60]=[C:59]([C:61]([F:64])([F:63])[F:62])[CH:58]=[CH:57][N:56]=2)[CH:53]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 739492-OxazolidinoneHCID 2724699PyBOPHCID 118092560HCID 118092560, compound

Product 1

HCID 118092731HCID 118092731, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DMF (800 μL), 1,3-oxazolidin-2-one (28 mg, 0.32 mmol), triethylamine (67 μL, 0.48 mmol) and (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (100 mg, 0.19 mmol) were added to 5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-2-carboxylic acid (60 mg, 0.16 mmol) and the reaction was stirred for 60 hours at room temperature. The reaction mixture was then diluted with water and extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase HPLC (10-80% acetonitrile/water with 0.1% TFA) and then chromatography on silica gel (10-100% acetone gradient in hexanes) to afford 3-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]carbonyl}-1,3-oxazolidin-2-one. MS ESI calc'd for C21H17F3N5O3 [M+H]+ 444. found 444. 1H NMR (500 MHz, DMSO-d6) δ 10.31 (s, 1H), 8.87-8.77 (m, 2H), 8.13 (dd, J=2.2 Hz, 8.1, 1H), 8.02 (s, 1H), 7.74 (d, J=8.1 Hz, 1H), 7.60 (s, 1H), 7.31-7.21 (m, 2H), 4.49 (t, J=7.8 Hz, 2H), 4.11 (t, J=7.8 Hz, 2H), 2.37 (s, 3H).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by reverse phase HPLC (10-80% acetonitrile/water with 0.1% TFA)

Sources & evidence

ORD record
ord-b918ce991144464e8dca12fd5284b814
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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