L-Valine → HCID 44476488, compound

HRID 2192520Notes

Reaction equation

HRID 2192520 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[H-].[Na+].Cl[C:12]1[C:21]2[C:16](=[C:17]([C:22]3[N:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH:34]([CH3:36])[CH3:35])=[C:29]([Cl:37])[CH:28]=4)[O:24][N:23]=3)[CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][N:13]=1>CS(C)=O.C(Cl)Cl>[Cl:37][C:29]1[CH:28]=[C:27]([C:25]2[O:24][N:23]=[C:22]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:16]=3[CH:15]=[CH:14][N:13]=[C:12]4[NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])[N:26]=2)[CH:32]=[CH:31][C:30]=1[O:33][CH:34]([CH3:36])[CH3:35]

Participants

6

Reactant 3

HCID 6287L-ValineHCID 24758Sodium hydrideHCID 58149900HCID 58149900, compound

Product 1

HCID 44476488HCID 44476488, compoundYield 36.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of L-valine (36.6 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 min. 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 stirred at 120° C. under nitrogen for 48 hr. The cooled reaction mixture was loaded onto an SCX column. The column was flushed with acetonitrile and then the desired product was eluted with 20% ammonia in acetonitrile. The solvent was removed in vacuo from the appropriate fractions to give an orange solid which was dissolved in DCM and washed with water. The organics were passed through a hydrophobic frit and the solvent was removed in vacuo to give the title compound as an orange solid (22 mg). MS (ES) C25H2535ClN4O4 requires 480. found 481 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred at 120° C. under nitrogen for 48 hr
  2. customThe cooled reaction mixture
  3. customThe column was flushed with acetonitrile
  4. washthe desired product was eluted with 20% ammonia in acetonitrile
  5. customThe solvent was removed in vacuo from the appropriate fractions
  6. customto give an orange solid which
  7. washwashed with water
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-590ff123e2104f6e8ba0aab06ac9c3ef
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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