4-Methylmorpholine → HCID 70564244, compound

HRID 1477868Notes

Reaction equation

HRID 1477868 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-c134f6dfbbd148fc98630b1969fc86dd
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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