4-Methylmorpholine → HCID 70564837, compound

HRID 1477894Notes

Reaction equation

HRID 1477894 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C:11]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)([CH2:16][CH2:17][F:18])[C:12]([O:14][CH3:15])=[O:13].CN1CCOCC1.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([C:11]([N:6]2[C:7]3[C:3](=[C:2]([NH:1][S:34]([CH3:33])(=[O:36])=[O:35])[CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:5]2)([CH2:16][CH2:17][F:18])[C:12]([O:14][CH3:15])=[O:13])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 70562272HCID 70562272, compound

Product 1

HCID 70564837HCID 70564837, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of compound from step B (68 mg, 0.189 mmol) and NMM (38 mg, 0.37 mmol) in DCM (7 mL) was added methylsulfonyl chloride (32 mg, 0.283 mmol) dropwise. Then the mixture was stirred at room temperature for 4 h. The reaction was quenched with saturated ammonium chloride solution, extracted with ethyl acetate (50 mL). The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with PE/EA (10/1 to 3/1, v/v) to afford the title compound as a white solid. LC/MS m/z=439.0[M+H]+.

Workup

  1. customThe reaction was quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate (50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with PE/EA (10/1 to 3/1

Sources & evidence

ORD record
ord-940a52dbdc524bd6b1d946f56582726a
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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