Sodium hydride → HCID 44476404, compound

HRID 2192516Notes

Reaction equation

HRID 2192516 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]1.[H-].[Na+].Cl[C:11]1[C:20]2[C:15](=[C:16]([C:21]3[N:25]=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH:33]([CH3:35])[CH3:34])=[C:28]([Cl:36])[CH:27]=4)[O:23][N:22]=3)[CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][N:12]=1>CS(C)=O>[NH4+:1].[Cl:36][C:28]1[CH:27]=[C:26]([C:24]2[O:23][N:22]=[C:21]([C:16]3[CH:17]=[CH:18][CH:19]=[C:20]4[C:15]=3[CH:14]=[CH:13][N:12]=[C:11]4[N:1]3[CH2:4][CH:3]([C:5]([O-:7])=[O:6])[CH2:2]3)[N:25]=2)[CH:31]=[CH:30][C:29]=1[O:32][CH:33]([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 931923-azetidinecarboxylic AcidHCID 58149900HCID 58149900, compound

Product 1

HCID 44476404HCID 44476404, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3-azetidinecarboxylic acid (Aldrich; 27.8 mg, 0.275 mmol), sodium hydride (60%; 8.79 mg, 0.220 mmol) in dimethyl sulfoxide (DMSO) (2 ml) was stirred at room temperature for 30 mins. 1-Chloro-5-(5-{3-chloro-4[(1methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)isoquinoline (D7; 44 mg, 0.110 mmol) was then added and the reaction mixture was heated to 120° C. under nitrogen overnight. The cooled reaction mixture was loaded onto a 10 g SCX column and eluted with acetonitrile followed by 10% ammonia in acetonitrile. The ammonia fractions were combined and evaporated and the residue was dissolved in dichloromethane and then 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 a yellow solid (9 mg)

Workup

  1. temperaturethe reaction mixture was heated to 120° C. under nitrogen overnight
  2. customThe cooled reaction mixture
  3. washeluted with acetonitrile
  4. customevaporated
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washwashed with water
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-eb7fb4b627af4ac8b8b9ea1d629efaf3
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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