Diisopropylethylamine → HCID 86628361, compound

HRID 2233172Notes

Reaction equation

HRID 2233172 reaction equation
[F:1][C:2]1[C:3]([CH:14]([CH2:30]O)[CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:18][CH2:17]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([O:12]C)=[N:5]2.CS(OS(C)(=O)=O)(=O)=O.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6](=[O:12])[N:5]3[CH2:30][CH:14]([CH2:15][N:16]4[CH2:21][CH2:20][CH:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:18][CH2:17]4)[C:3]=1[C:4]=23

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 86628360HCID 86628360, compound

Product 1

HCID 86628361HCID 86628361, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1,1-dimethylethyl (1-{2-[6-fluoro-3-(methyloxy)-5-quinoxalinyl]-3-hydroxypropyl}-4-piperidinyl)carbamate (10.8 g, 25 mmol), methanesulfonic anhydride (5.12 g, 28.7 mmol) and N,N-diisopropylethylamine (9.8 ml, 56 mmol) in dry chloroform (140 ml) was stirred at room temperature for 0.5 h, then heated under reflux for 3 days. The mixture was washed with aqueous sodium bicarbonate and the aqueous phase was extracted with dichloromethane. The combined organic fractions were dried and evaporated. The residue was chromatographed on silica (500 g), eluting with 0-5% methanol/dichloromethane to give the product (8.13 g, 81%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 days
  3. washThe mixture was washed with aqueous sodium bicarbonate
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. customThe combined organic fractions were dried
  6. customevaporated
  7. customThe residue was chromatographed on silica (500 g)
  8. washeluting with 0-5% methanol/dichloromethane

Sources & evidence

ORD record
ord-34d66e4df4c946d6a43ba0094d8fb102
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

Loading…