4-Methylmorpholine → HCID 70561240, compound

HRID 1427307Notes

Reaction equation

HRID 1427307 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:13]2[C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([NH2:22])[C:16]=3[CH:15]=[CH:14]2)([CH2:11][CH3:12])[CH:9]=[CH2:10])=[CH:4][CH:3]=1.CN1CCOCC1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:13]2[C:21]3[C:16](=[C:17]([NH:22][S:31]([CH3:30])(=[O:33])=[O:32])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)([CH2:11][CH3:12])[CH:9]=[CH2:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 70560764HCID 70560764, compound

Product 1

HCID 70561240HCID 70561240, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Step B (40 mg, 0.128 mmol) and N-methylmorpholine (26 mg, 0.256 mmol) in dichloromethane (2 mL) was added methanesulfonyl chloride (18 mg, 0.192 mmol) at room temperature. The mixture was stirred for 2 h, then diluted with water (10 mL) and extracted with ethyl acetate. The combined organic layers were washed with brine (10 mL), dried over Na2SO4, filtered and concentrated. The crude product was purified by PREP-TLC eluting with PE/EA (3/1, v/v) to give the title compound as a colorless solid. LC/MS m/z=388.9 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified
  7. washby PREP-TLC eluting with PE/EA (3/1

Sources & evidence

ORD record
ord-748eec07dcb9461f87d43f7b0d35420f
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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