4-Methylmorpholine → Methyl 3-(4-chlorophenyl)-3-(4-(methylsulfonamido)-1H-indol-1-yl)pentanoate

HRID 1477916Notes

Reaction equation

HRID 1477916 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)([CH2:17][CH3:18])[CH2:12][C:13]([O:15][CH3:16])=[O:14].CN1CCOCC1.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl>[Cl:25][C:22]1[CH:23]=[CH:24][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)([CH2:17][CH3:18])[CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 68175795Methyl 3-(4-amino-1H-indol-1-yl)-3-(4-chlorophenyl)pentanoate

Product 1

HCID 70564698Methyl 3-(4-chlorophenyl)-3-(4-(methylsulfonamido)-1H-indol-1-yl)pentanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of the product of Step G (75 mg, 0.21 mmol) and NMM (42 mg, 0.42 mmol) in DCM (3 mL) was added methanesulfonyl chloride (36 mg, 0.38 mmol). Then the mixture was stirred at room temperature for 3 h, quenched with saturated ammonium chloride solution, and extracted with ethyl acetate. The organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (PE/EA=3/1) to afford the title compound as colorless oil. LC/MS m/z=435.1[M+H]+.

Workup

  1. customquenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layers were washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography (PE/EA=3/1)

Sources & evidence

ORD record
ord-825dc7d2089b4917b702e67ca93a4543
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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