Acetic Anhydride → HCID 25104296, compound

HRID 238548Notes

Reaction equation

HRID 238548 reaction equation
Cl.[CH3:2][N:3]([CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[C:4]([C:6]1[CH:14]=[CH:13][C:9]2=[N:10][O:11][N:12]=[C:8]2[CH:7]=1)=[O:5].C1C[O:24][CH2:23]C1.C(N(CC)CC)C.C(OC(=O)C)(=O)C>C(Cl)(Cl)Cl.C(O)=O>[CH:23]([N:18]1[CH2:19][CH2:20][CH:15]([N:3]([CH3:2])[C:4]([C:6]2[CH:14]=[CH:13][C:9]3=[N:10][O:11][N:12]=[C:8]3[CH:7]=2)=[O:5])[CH2:16][CH2:17]1)=[O:24]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 25104291HCID 25104291, compound

Product 1

HCID 25104296HCID 25104296, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6212ChloroformSolvent

Procedure

N-Methyl-N-piperidin-4-yl-[2,1,3]-benzoxadiazole-5-carboxamide hydrochloride (0.5 g, 1.7 mmol) was suspended in chloroform (20 ml) and THF (20 ml) and triethylamine (6 ml), was added. A mixture of formic acid (1 ml) and acetic anhydride (1 ml) was stirred for 1.5 h at room temperature and then slowly added to the suspension. After stirring the mixture for 1 h, it was washed with water (100 ml) and H2SO4 (→pH 2) and NaHCO3 solution (100 ml). The aqueous was extracted with chloroform (2×100 ml) and the combined organics were dried (MgSO4), concentrated under vacuum, and purified by silica gel chromatography, eluting with ethyl acetate/chloroform/methanol (50:45:5) to give a white solid (341 mg). Mp=163-165° C., 1H NMR (300 MHz, CDCl3) δ 8.05 (s, 1H), 7.93 (d, J=9.3 Hz, 1H); 7.86 (s, 1H); 7.42 (d, J=9.3 Hz, 1H); 4.90-4.45 and 3.85-2.60 (m, 5H); 2.88 (sb, 3H); and 1.95-1.60 ppm (m, 4H).

Workup

  1. additionslowly added to the suspension
  2. stirringAfter stirring the mixture for 1 h
  3. washit was washed with water (100 ml) and H2SO4 (→pH 2) and NaHCO3 solution (100 ml)
  4. extractionThe aqueous was extracted with chloroform (2×100 ml)
  5. dry with materialthe combined organics were dried (MgSO4)
  6. concentrationconcentrated under vacuum
  7. custompurified by silica gel chromatography
  8. washeluting with ethyl acetate/chloroform/methanol (50:45:5)

Sources & evidence

ORD record
ord-b9e6df2ce42f4e008973b7cba2063a7b
Source dataset
uspto-grants-2014_02
Patent number
US08642633B2

Reaction notes

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