Dimethyl Sulfoxide → HCID 44476407, compound

HRID 2192518Notes

Reaction equation

HRID 2192518 reaction equation
[H-].[Na+].CS(C)=O.[NH:7]1[CH2:14][CH2:13][CH2:12][C@H:8]1[C:9]([OH:11])=[O:10].Cl[C:16]1[C:25]2[C:20](=[C:21]([C:26]3[N:30]=[C:29]([C:31]4[CH:36]=[CH:35][C:34]([O:37][CH:38]([CH3:40])[CH3:39])=[C:33]([Cl:41])[CH:32]=4)[O:28][N:27]=3)[CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][N:17]=1>C(Cl)Cl>[Cl:41][C:33]1[CH:32]=[C:31]([C:29]2[O:28][N:27]=[C:26]([C:21]3[CH:22]=[CH:23][CH:24]=[C:25]4[C:20]=3[CH:19]=[CH:18][N:17]=[C:16]4[N:7]3[CH2:14][CH2:13][CH2:12][C@H:8]3[C:9]([OH:11])=[O:10])[N:30]=2)[CH:36]=[CH:35][C:34]=1[O:37][CH:38]([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 145742L-ProlineHCID 58149900HCID 58149900, compound

Product 1

HCID 44476407HCID 44476407, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of sodium hydride (60%; 9.99 mg, 0.250 mmol), dimethyl sulfoxide (DMSO) (2 ml) and proline (36.0 mg, 0.312 mmol) were stirred at room temp under nitrogen for 1 hour. 1-Chloro-5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)isoquinoline (D7; 50 mg, 0.125 mmol) was added and the reaction mixture was heated at 120° C. under nitrogen for 3 hr. The cooled reaction mixture was loaded onto an SCX column. The column was washed with methanol and then eluted using 2M methanolic ammonia. The appropriate fractions were combined and the solvent was removed in vacuo to give an orange oil which was dissolved in DCM and washed with water. The organic phase was passed through a hydrophobic frit and the solvent was removed in vacuo to give the title compound as an orange solid (40 mg).

Workup

  1. temperaturethe reaction mixture was heated at 120° C. under nitrogen for 3 hr
  2. customThe cooled reaction mixture
  3. washThe column was washed with methanol
  4. washeluted
  5. customthe solvent was removed in vacuo
  6. customto give an orange oil which
  7. washwashed with water
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d504dd9b378942ddbc54be05ca3e8ec6
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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