4-Methylmorpholine → HCID 70564704, compound

HRID 1477924Notes

Reaction equation

HRID 1477924 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[C:11]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)([CH2:18][CH3:19])/[CH:12]=[CH:13]/[C:14]([O:16][CH3:17])=[O:15].CN1CCOCC1.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:11]([N:6]2[C:7]3[C:3](=[C:2]([NH:1][S:35]([CH3:34])(=[O:37])=[O:36])[CH:10]=[CH:9][CH:8]=3)[CH:4]=[N:5]2)([CH2:18][CH3:19])/[CH:12]=[CH:13]/[C:14]([O:16][CH3:17])=[O:15])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 70564872HCID 70564872, compound

Product 1

HCID 70564704HCID 70564704, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (E)-methyl 4-(4-amino-1H-indazol-1-yl)-4-(4-chlorophenyl)hex-2-enoate (120 mg) and NMM (98 mg) in DCM (5 mL) was added MsCl (45 mg). Then the mixture was stirred at room temperature for 2 h. The solution was quenched with saturated NH4Cl solution, and extracted with ethyl acetate (30 mL). The organic layer was washed with brine, dried over dry sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (PE/EA=5/1) to afford the title compound as a pale yellow solid. LC/MS m/z=448.2[M+H]+.

Workup

  1. customThe solution was quenched with saturated NH4Cl solution
  2. extractionextracted with ethyl acetate (30 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over dry sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography (PE/EA=5/1)

Sources & evidence

ORD record
ord-a6a8a60f0d6f4f66bddb89597c41a59e
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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