Methylamine → HCID 9857098, compound

HRID 884447Notes

Reaction equation

HRID 884447 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[C:5]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:4]=1.[CH3:19][NH2:20]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:20][CH3:19])(=[O:11])=[O:10])=[C:5]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:4]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 9814569HCID 9814569, compound

Product 1

HCID 9857098HCID 9857098, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-methoxy-2-morpholin-4-yl-benzenesulfonyl chloride (37 mg; 0.13 mmol) in dry CH2Cl2 (1 mL) was added methylamine (0.16 mL of 2.0 M solution in tetrahydrofuran; 0.32 mmol) via syringe at room temperature under a nitrogen atmosphere. After stirring for 15 hours, the reaction was diluted with CH2Cl2 (25 mL), washed with water, saturated aqueous NaHCO3 and brine, then dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified via HPLC (Biotage with 2:1 hexanes/EtOAc) to provide the sulfonamide as a white solid (12.5 mg; 34%).

Workup

  1. washwashed with water, saturated aqueous NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via HPLC (Biotage with 2:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-c11cb634767242be8c401213ff729b09
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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