Sodium hydride → HCID 178523756, compound

HRID 2391007Notes

Reaction equation

HRID 2391007 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([N:6]2[CH2:10][CH2:9][NH:8][C:7]2=[O:11])=[N:2]1.[H-].[Na+].CC1C=CC(S(O[CH2:25][C@H:26]2[CH2:31][CH2:30][C@H:29]([NH:32][C:33](=[O:45])[C:34]3[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[CH:36][C:35]=3[Cl:44])[CH2:28][CH2:27]2)(=O)=O)=CC=1>C(#N)C>[Cl:44][C:35]1[CH:36]=[CH:37][C:38]([C:40]([F:41])([F:42])[F:43])=[CH:39][C:34]=1[C:33]([NH:32][C@H:29]1[CH2:30][CH2:31][C@H:26]([CH2:25][N:1]2[CH:5]=[CH:4][C:3]([N:6]3[CH2:10][CH2:9][NH:8][C:7]3=[O:11])=[N:2]2)[CH2:27][CH2:28]1)=[O:45]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 178427755HCID 178427755, compoundHCID 178517829HCID 178517829, compound

Product 1

HCID 178523756HCID 178523756, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(1H-pyrazol-3-yl)imidazolidin-2-one (410 mg, 2.69 mmol) is placed in a microwave vial with acetonitrile (12 mL). NaH (60%, 108 mg, 2.69 mmol) is added and the reaction mixture is stirred at RT for 30 minutes. Trans-(4-(2-chloro-5-(trifluoromethyl)benzamido)cyclohexyl)methyl 4-methylbenzenesulfonate (1.20 g (0.20 mmol) is added and the mixture is heated using microwave radiation at 120° C. for 30 minutes. The mixture is partitioned between DCM and water. The organic phase is washed with water and brine, dried over MgSO4, filtered and the solvent was removed in vacuo. The product is purified by crystallization (EtOAc with a small amount of MeOH) to afford the title compound.

Workup

  1. temperaturethe mixture is heated
  2. customat 120° C.
  3. customfor 30 minutes
  4. customThe mixture is partitioned between DCM and water
  5. washThe organic phase is washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customThe product is purified by crystallization (EtOAc with a small amount of MeOH)

Sources & evidence

ORD record
ord-f9eefca19c91422cbd4963677c4f8454
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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