Triethylamine → HCID 25104297, compound

HRID 238549Notes

Reaction equation

HRID 238549 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].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)(Cl)Cl>[CH3:2][N:3]([CH:15]1[CH2:20][CH2:19][N:18]([S:29]([CH3:28])(=[O:31])=[O:30])[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]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 25104291HCID 25104291, compound

Product 1

HCID 25104297HCID 25104297, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
20 °C

Procedure

N-Methyl-N-piperidin-4-yl-[2,1,3]-benzoxadiazole-5-carboxamide hydrochloride (0.38 g, 1.3 mmol) was suspended in chloroform (70 ml) and triethylamine (2 ml) was added. A solution of methane sulfonyl chloride (0.14 g, 1.26 mmol) in chloroform (10 ml) was added and the mixture was stirred at 20° C. for 2 h. The mixture was washed with water (50 ml) and H2SO4 (→pH 2) and NaHCO3 solution (50 ml) and the aqueous re-extracted with dichloromethane (2×50 ml). The combined organics were dried (MgSO4), concentrated under vacuum, and the crude product was purified on a silica gel column eluting with dichloromethane/THF (85:15) to give a white crystalline product, after crystallization from MTBE/hexane (204 mg). Mp=177-179° C., 1H NMR (300 MHz, CDCl3) δ 7.93 (d, J=9.3 Hz, 1H); 7.85 (s, 1H); 7.42 (d, J=9.3 Hz, 1H); 4.75-4.46 and 4.10-3.90 and 3.10-2.40 (m, 5H); 2.92 (s, 3H), 2.83 (s, 3H) and 2.10-1.70 ppm (m, 4H).

Workup

  1. washThe mixture was washed with water (50 ml) and H2SO4 (→pH 2) and NaHCO3 solution (50 ml)
  2. extractionthe aqueous re-extracted with dichloromethane (2×50 ml)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. concentrationconcentrated under vacuum
  5. customthe crude product was purified on a silica gel column
  6. washeluting with dichloromethane/THF (85:15)
  7. customto give a white crystalline product
  8. customafter crystallization from MTBE/hexane (204 mg)

Sources & evidence

ORD record
ord-eab1602442d340cd9f062b9180b263dc
Source dataset
uspto-grants-2014_02
Patent number
US08642633B2

Reaction notes

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