Dimethyl Sulfoxide → HCID 21994132, compound

HRID 1978421Notes

Reaction equation

HRID 1978421 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([CH2:29][N:30]1[CH2:35][CH2:34][CH:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:32][CH2:31]1)[CH2:13][NH:14][C:15]([C:17]1[S:27][C:26]2[N:28]3[C:19](=[CH:20][N:21]=[C:22]3[CH:23]=[CH:24][CH:25]=2)[CH:18]=1)=[O:16].C(N(CC)CC)C>ClCCl.O>[O:11]=[C:12]([CH2:29][N:30]1[CH2:35][CH2:34][CH:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:32][CH2:31]1)[CH2:13][NH:14][C:15]([C:17]1[S:27][C:26]2[N:28]3[C:19](=[CH:20][N:21]=[C:22]3[CH:23]=[CH:24][CH:25]=2)[CH:18]=1)=[O:16]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 21993732HCID 21993732, compound

Product 1

HCID 21994132HCID 21994132, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 0.39 g (3.05 mM) of oxalyl chloride in 20 ml of dichloromethane was added 0.43 ml (6.11 mM) of dimethyl sulfoxide dropwise at −78° C. The mixture was stirred for 5 minutes, at the end of which time a solution of 0.885 g (2.037 mM) of N-[2-hydroxy-3-(4-phenylpiperidino)propan-1-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide in 20 ml of dichloromethane was added and the mixture was stirred at −78° C. for 15 minutes. To this mixture was added 1.70 ml (12.2 mM) of triethylamine and the temperature was increased to room temperature. This reaction mixture was poured in water and extracted with 3 portions of ethyl acetate. The organic layers were pooled and dried over MgSO4 and the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate-methanol=9/1 to 4/1) to provide the title compound.

Workup

  1. additionwas added
  2. temperaturethe temperature was increased to room temperature
  3. extractionextracted with 3 portions of ethyl acetate
  4. dry with materialdried over MgSO4
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate-methanol=9/1 to 4/1)

Sources & evidence

ORD record
ord-66713151ad3b4a0697c36c9589a8100f
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

Loading…