Benzoic Acid → HCID 60962724, compound

HRID 2380971Notes

Reaction equation

HRID 2380971 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:11]1([CH:17]2[O:22][CH2:21][CH2:20][NH:19][CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([N:25](CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C.ClCCl>[NH2:25][C:5]1[CH:6]=[CH:7][C:2]([C:1]([N:19]2[CH2:20][CH2:21][O:22][CH:17]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:18]2)=[O:9])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 123435392-Phenylmorpholine--hydrogen chloride (1/1)

Product 1

HCID 60962724HCID 60962724, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of benzoic acid (160 mg, 1 mmol) and 2-phenylmorpholine hydrochloride (300 mg, 1.5 mmol) in acetonitrile (10 ml) was added triethylamine (0.4 ml, 3 mmol) followed by HATU and the reaction mixture was stirred at room temperature for 16 hours. The reaction was diluted with dichloromethane (25 ml) and washed with sodium hydrogen carbonate (25 ml, saturated solution). The organics were collected, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with ethylacetate to afford the title compound as a clear oil (240 mg, 84% yield). HPLC retention time 5.05 min. Mass spectrum (ES+) m/z 283 (M+H).

Workup

  1. washwashed with sodium hydrogen carbonate (25 ml, saturated solution)
  2. customThe organics were collected
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel
  6. washeluting with ethylacetate

Sources & evidence

ORD record
ord-dda36f40f4ba44969869b63ef25201cf
Source dataset
uspto-grants-2012_09
Patent number
US08258138B2

Reaction notes

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