Cesium carbonate → HCID 25013658, compound

HRID 2093475Notes

Reaction equation

HRID 2093475 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:30]1[O:31][C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=1>CN1C(=O)CCC1.C(=O)(O)[O-].[Na+]>[O:31]1[C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=[C:30]1[N:20]1[CH2:21][CH2:22][CH:17]([CH:14]2[CH2:15][CH2:16][N:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=3)[CH2:12][CH2:13]2)[CH2:18][CH2:19]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 119862-ChlorobenzoxazoleHCID 591788671[4-(Methylsulfonyl)phenyl]-4,4'-bipiperidine

Product 1

HCID 25013658HCID 25013658, compound

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The 1[4-(methylsulfonyl)phenyl]-4,4′-bipiperidine (70 mg, 0.22 mmol) and cesium carbonate (212 mg, 0.65 mmol) were slurried in NMP (0.43 ml) and the Chlorobenzoxazole (20.3 mmol) added. The mixture was stirred at 120 C overnight. The slurry was diluted with 15% saturated sodium bicarbonate:water (40 ml) and extracted with DCM (3×25 ml). The combined organic fraction was washed with brine, dried over magnesium sulfate, filtered, and the volatiles removed in vac. The crude material was purified by chromatography on silica gel with 5% acetone:DCM to yield the titled compound. LRMS calc: 478.1 obs: 478.8, 480.8 (M+H).

Workup

  1. extractionwater (40 ml) and extracted with DCM (3×25 ml)
  2. washThe combined organic fraction was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe volatiles removed in vac
  6. customThe crude material was purified by chromatography on silica gel with 5% acetone

Sources & evidence

ORD record
ord-a3c1685eca2c46768ad90b7381b5a815
Source dataset
uspto-grants-2013_05
Patent number
US08445499B2

Reaction notes

Loading…