L-Alanine → HCID 44476406, compound

HRID 2192517Notes

Reaction equation

HRID 2192517 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[H-].[Na+].Cl[C:10]1[C:19]2[C:14](=[C:15]([C:20]3[N:24]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH:32]([CH3:34])[CH3:33])=[C:27]([Cl:35])[CH:26]=4)[O:22][N:21]=3)[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][N:11]=1>CS(C)=O>[Cl:35][C:27]1[CH:26]=[C:25]([C:23]2[O:22][N:21]=[C:20]([C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:14]=3[CH:13]=[CH:12][N:11]=[C:10]4[NH:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3])[N:24]=2)[CH:30]=[CH:29][C:28]=1[O:31][CH:32]([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 5950L-AlanineHCID 24758Sodium hydrideHCID 58149900HCID 58149900, compound

Product 1

HCID 44476406HCID 44476406, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of L-alanine (27.8 mg, 0.312 mmol) and sodium hydride (60%; 9.99 mg, 0.250 mmol) in dimethyl sulfoxide (DMSO) (2 ml) were stirred at room temp for 30 mins. 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 left to stir at 120° C. under nitrogen for 48 hrs. The reaction mixture was loaded onto a 10 g SCX column and washed with acetonitrile, then eluted with 10% ammonia in acetonitrile. The solvent was evaporated from the appropriate fractions and the residue was dissolved in dichloromethane 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 (29 mg)

Workup

  1. waitthe reaction mixture was left
  2. stirringto stir at 120° C. under nitrogen for 48 hrs
  3. washwashed with acetonitrile
  4. washeluted with 10% ammonia in acetonitrile
  5. customThe solvent was evaporated from the appropriate fractions
  6. dissolutionthe residue was dissolved in dichloromethane
  7. washwashed with water
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b35544adb7b24d9b853eb919a6083bd8
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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