4-Methylmorpholine → HCID 57524786, compound

HRID 1477831Notes

Reaction equation

HRID 1477831 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[C:16]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)([CH2:21][CH3:22])[C:17]([O:19][CH3:20])=[O:18].CN1CCOCC1>C(Cl)Cl>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([C:16]([N:11]2[C:12]3[C:8](=[C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:15]=[CH:14][CH:13]=3)[CH:9]=[CH:10]2)([CH2:21][CH3:22])[C:17]([O:19][CH3:20])=[O:18])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chloride2×HCID 70565237HCID 70565237, compound

Product 1

HCID 57524786HCID 57524786, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (1.59 mL, 20.4 mmol) was added to a stirred solution of 3b (6.67 g, 19.5 mmol) and 4-methylmorpholine (2.78 mL, 25.3 mmol) in DCM (100 mL) at 0° C. After 30 min, an additional portion of methanesulfonyl chloride (0.80 mL, 10.2 mmol) was added. After 1 h, the reaction mixture was partitioned between DCM and saturated aqueous ammonium chloride. The layers were separated and the aqueous layer was extracted with DCM. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-50% EtOAc/hexanes as eluent) to afford the title compound 25. m/z (ES) 421 (MH)+; IP=A rating

Workup

  1. waitAfter 1 h
  2. customthe reaction mixture was partitioned between DCM and saturated aqueous ammonium chloride
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM
  5. washThe combined organics were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-50% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-411e371d8025487983fae0b899947209
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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