Sodium hydride → HCID 58474761, compound

HRID 1400831Notes

Reaction equation

HRID 1400831 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:17][C:16]3[C:11](=[N:12][CH:13]=[CH:14][C:15]=3[O:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=3[F:28])[CH:10]=2)=[N:7][CH:8]=1.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][C:30]1=[O:35].[H-].[Na+]>C1COCC1>[F:28][C:20]1[CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=[CH:24][C:19]=1[O:18][C:15]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:10]=[C:9]([C:6]3[N:7]=[CH:8][C:3]([CH2:2][N:29]4[CH2:34][CH2:33][O:32][CH2:31][C:30]4=[O:35])=[CH:4][CH:5]=3)[S:17][C:16]=12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 669533-MorpholinoneHCID 58474527HCID 58474527, compound

Product 1

HCID 58474761HCID 58474761, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 102 (350 mg, 0.842 mmol, scheme 26) in THF (10 mL) was added a solution of the anion [made from morpholin-3-one (340 mg, 4 eq., 3.37 mmol) and NaH (81 mg, 4 eq., 3.37 mmol)] in THF (5 mL)) and the mixture was heated to reflux for 8 hours. The mixture was quenched with saturated NH4Cl solution and extracted with DCM. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated. The resultant solid was triturated with acetone to give title compound 121 (135 mg, 33% yield) which was used in the next step with no additional purification. MS (m/z)=481.2 (M+H)

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 8 hours
  3. customThe mixture was quenched with saturated NH4Cl solution
  4. extractionextracted with DCM
  5. customThe organic phase was collected
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resultant solid was triturated with acetone

Sources & evidence

ORD record
ord-931cfadd6c184d27854ec83bce18be16
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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