4-Methylmorpholine → HCID 10410852, compound

HRID 425923Notes

Reaction equation

HRID 425923 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([O:15][CH2:16][C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])[C:11]([NH2:14])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].CN1CCOCC1>C(Cl)Cl.C(OCC)(=O)C>[NH2:14][C:11]1[N:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:26]([CH3:25])(=[O:28])=[O:27])=[CH:3][CH:4]=2)=[CH:9][C:10]=1[O:15][CH2:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:24]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 10451121HCID 10451121, compound

Product 1

HCID 10410852HCID 10410852, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(4-amino-phenyl)-3-(2,6-dichloro-benzyloxy)-pyridin-2-ylamine (100 mg, 0.28 mmol) in methylene chloride (5 mL) at 0° C., was added methanesulfonyl chloride (0.021 mL, 0.28 mmol) and 4-methylmorpholine (0.16 mL). The mixture was stirred at room temperature for 2 hr, and diluted with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified with a silica gel column eluting with hexane-ethyl acetate (5:1) to give N-{4-[6-amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-phenyl}-methanesulfonamide.

Workup

  1. washThe organic layers were washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified with a silica gel column
  5. washeluting with hexane-ethyl acetate (5:1)

Sources & evidence

ORD record
ord-1c01616b4c164d6891754e10dd5fa30f
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

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