Benzylamine → HCID 1472700, compound

HRID 2367160Notes

Reaction equation

HRID 2367160 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([C:12]([C:14]3[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=3[C:16]([OH:18])=O)=[O:13])[CH:10]=[CH:11][C:5]=2[O:4][CH2:3]1.CN1CCOCC1.C1C=NC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:64]([NH2:71])[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>CN(C)C=O>[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([C:12]([C:14]3[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=3[C:16]([NH:71][CH2:64][C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[O:18])=[O:13])[CH:10]=[CH:11][C:5]=2[O:4][CH2:3]1

Participants

7

Reactant 5

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 181649HOAtHCID 17174602-(3-Oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 1472700HCID 1472700, compoundYield 211.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-yl)carbonylbenzoic acid (100 mg, 033 mmol) in N,N-dimethylformamide (2.00 mL) was added N-methylmorpholine (0.14 mL 1.32 mmol) followed by addition of HOAt (55 mg, 0.40 mmol) and HATU (130 mg, 0.33 mmol). The mixture was stirred for 30 minutes at room temperature followed by the addition of benzylamine (36 uL, 0.33 mmol). The reaction mixture was then heated to 60° C. for 18 h. The mixture was cooled to room temperature and the solvent was evaporated. The residue was dissolved in ethyl acetate the organic layer was washed with brine, 1.0 M aq. hydrochloric acid, brine, saturated aq. sodium-hydrogencarbonate and brine. The organic layer was separated dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by column chromatography (SiO2, hexanes/ethyl acetate) to afford the title compound (0.27 g, 80%). MS (EI) for C23H18N2O4: 387 (M+H).

Workup

  1. temperatureThe reaction mixture was then heated to 60° C. for 18 h
  2. temperatureThe mixture was cooled to room temperature
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate the organic layer
  5. washwas washed with brine, 1.0 M aq. hydrochloric acid, brine, saturated aq. sodium-hydrogencarbonate and brine
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated in vacuo
  10. customThe residue was purified by column chromatography (SiO2, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-7f0dba3f61244c2daba24074ab1389ff
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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