4-Methylmorpholine → HCID 70564244, compound

HRID 1427240Notes

Reaction equation

HRID 1427240 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:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)([CH2:15][CH3:16])[CH2:12][C:13]#[N:14].CN1CCOCC1.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl.O>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([C:11]([N:6]2[C:7]3[C:3](=[C:2]([NH:1][S:32]([CH3:31])(=[O:34])=[O:33])[CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:5]2)([CH2:15][CH3:16])[CH2:12][C:13]#[N:14])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 70565327HCID 70565327, compound

Product 1

HCID 70564244HCID 70564244, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Step D (170 mg, 0.52 mmol) and N-methylmorpholine (105 mg, 1.04 mmol) in dichloromethane (15 mL) was added methanesulfonyl chloride (89 mg, 0.79 mmol) at room temperature. The mixture was stirred for 2 h, then diluted with water (15 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 amorphous solid. LC/MS m/z=402.1 [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-3c8455979e0a4f3ea0b57686f29bcecd
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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