Ethyl Acetate → HCID 58026771, compound

HRID 909296Notes

Reaction equation

HRID 909296 reaction equation
O[C:2]1[C:7]([C:8]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(OCC)(=O)C>CN(C)C=O>[N+:17]([C:14]1[CH:15]=[CH:16][C:8]2[C:7]3[C:2](=[N:3][CH:4]=[CH:5][CH:6]=3)[O:11][C:10](=[O:12])[C:9]=2[CH:13]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524574HCID 178524574, compound

Product 1

HCID 58026771HCID 58026771, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(2-Hydroxypyridin-3-yl)-5-nitrobenzoic acid (Reference Compound No. 1-3-(3), 50 mg, 0.20 mmol) was dissolved in N,N-dimethylformamide (5 mL), then N,N-diisopropylethylamine (141 μL, 0.81 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (154 mg, 0.41 mmol) were added thereto, and then the reaction mixture was stirred at room temperature overnight. Ethyl acetate (30 mL) was added to the reaction mixture, the whole was washed with water (30 mL) and saturated brine (30 mL) successively. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. Chloroform was added to the obtained residue, and then filtered to give the titled reference compound (35 mg) as a pale yellow solid. (Yield 71%)

Workup

  1. washthe whole was washed with water (30 mL) and saturated brine (30 mL) successively
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. additionChloroform was added to the obtained residue
  5. filtrationfiltered

Sources & evidence

ORD record
ord-9dcce231a0e14461852ddf8b12c6d74d
Source dataset
uspto-grants-2011_09
Patent number
US08017775B2

Reaction notes

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