Potassium Carbonate → HCID 178482456, compound

HRID 1510163Notes

Reaction equation

HRID 1510163 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C@@:12]3([CH2:17][CH2:16][NH:15][C@@H:14]([CH3:18])[CH2:13]3)[C:11]([NH:19][CH3:20])=[N:10][C:9]2=[O:21])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[I:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32]Br>CS(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C@@:12]3([CH2:17][CH2:16][N:15]([CH2:32][C:31]4[CH:34]=[CH:35][CH:36]=[C:29]([I:28])[CH:30]=4)[C@@H:14]([CH3:18])[CH2:13]3)[C:11]([NH:19][CH3:20])=[N:10][C:9]2=[O:21])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27593613-Iodobenzyl bromideHCID 178482458HCID 178482458, compound

Product 1

HCID 178482456HCID 178482456, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

(5R,7S)-1-(3-fluorophenyl)-7-methyl-4-(methylamino)-1,3,8-triazaspiro[4.5]dec-3-en-2-one (250 mg, 0.86 mmol) from step 2 above was dissolved in DMSO (8.0 mL). The flask was charged with K2CO3 (594 mg, 4.30 mmol) and 3-iodo-benzylbromide (255 mg, 0.86 mmol). The mixture was then sealed with a septum and placed in 50° C. oil bath and allowed to stir overnight. The mixture was diluted with water and extracted with EtOAc (three times). The combined organic layers were washed with aqueous LiCl (three times), followed by brine and then dried over Na2SO4. Solvent removal under reduced pressure gave crude product. Purification over silica via automated flash chromatography (0 to 20% MeOH/CH2Cl2 over 20 min.) gave after solvent removal the product as a white solid: LCMS [M+H]=507.3

Workup

  1. customThe mixture was then sealed with a septum
  2. customplaced in 50° C.
  3. extractionextracted with EtOAc (three times)
  4. washThe combined organic layers were washed with aqueous LiCl (three times)
  5. dry with materialdried over Na2SO4
  6. customSolvent removal under reduced pressure
  7. customgave crude product
  8. customPurification over silica via automated flash chromatography (0 to 20% MeOH/CH2Cl2 over 20 min.)
  9. customgave
  10. customafter solvent removal the product as a white solid

Sources & evidence

ORD record
ord-aad53f562ad242e6aef25ece4d9870f6
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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