Dimethyl Sulfoxide → HCID 13185701, compound

HRID 1036375Notes

Reaction equation

HRID 1036375 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]2[CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([OH:22])[C:12]=12.C(N(CC)CC)C>ClCCl>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]2[CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:22])[C:12]=12

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 584218HCID 584218, compound

Product 1

HCID 13185701HCID 13185701, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of oxalyl chloride (1 mL) in dichloromethane, cooled to −78° C. was added dropwise a solution of dimethyl sulfoxide (1.5 mL) in dichloromethane. The mixture was stirred for 10 minutes and a solution of 6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol (Chem. Pharm. Bull. 43, 3, 1995), (1.42 g, 8.7 mmol) in dichloromethane was added to it. After 30 minutes, triethylamine (6 mL) was added to the reaction mixture and it was stirred at ambient temperature for 1 hour and partitioned in dichloromethane/water. The organic layer was dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel, eluting with ethyl acetate to yield the title compound: 1H NMR (300 MHz, CDCl3) δ 8.64 (dd, J=4.58, 1.53 Hz, 1 H), 7.58 (dd, J=7.63, 1.53 Hz, 1 H), 7.33 (dd, J=7.80, 4.75 Hz, 1 H), 2.92 (m, 2 H), 2.80 (m, 2 H), 1.90 (s, 4 H); MS (DCI/NH3) m/z 162 (M+H)+.

Workup

  1. waitAfter 30 minutes
  2. stirringwas stirred at ambient temperature for 1 hour
  3. custompartitioned in dichloromethane/water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-8847ba7327cc40baae8fc532950f42b9
Source dataset
uspto-grants-2013_10
Patent number
US08546410B2

Reaction notes

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