4-Methylmorpholine → HCID 19603190, compound

HRID 650965Notes

Reaction equation

HRID 650965 reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([CH:11]2[C:17]3=[N:18][CH:19]=[C:20]([Br:22])[CH:21]=[C:16]3[CH2:15][CH2:14][C:13]3[CH:23]=[C:24]([Cl:28])[CH:25]=[C:26]([Cl:27])[C:12]2=3)[CH2:7][CH2:6]1)=[O:4].CN1CCOCC1.[S:36](Cl)([CH3:39])(=[O:38])=[O:37]>C(Cl)Cl>[Br:22][C:20]1[CH:21]=[C:16]2[CH2:15][CH2:14][C:13]3[CH:23]=[C:24]([Cl:28])[CH:25]=[C:26]([Cl:27])[C:12]=3[CH:11]([CH:8]3[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][NH:1][S:36]([CH3:39])(=[O:38])=[O:37])[CH2:6][CH2:7]3)[C:17]2=[N:18][CH:19]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 19603189HCID 19603189, compound

Product 1

HCID 19603190HCID 19603190, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound of Example 3 (0.15 g, 0.31 mmol) was dissolved in CH2Cl2 (1.5 mL). 4-Methylmorpholine (102 uL), followed by mesyl chloride (36 uL, 0.47 mmol, 1.5 equiv.) was then added. Reaction mixture was stirred at room tempearture ovemite. The CH2Cl2 phase was washed twice with Sat. NaHCO3, brine and then dried over Na2SO4. CH2Cl2 was then removed by rotary evaporation and resulting residue was purified on silica gel column eluting with 30% EtOAc/CH2Cl2 to give the title compound as a white solid (0.109 9, mp=120-140° C., MH+==562.

Workup

  1. additionwas then added
  2. customReaction mixture
  3. washThe CH2Cl2 phase was washed twice with Sat. NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. customCH2Cl2 was then removed by rotary evaporation
  6. customresulting residue
  7. customwas purified on silica gel column
  8. washeluting with 30% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-74da3100899b4199a4745ab86e8c2b8d
Source dataset
uspto-grants-2001_08
Patent number
US06277854B1

Reaction notes

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