4-Methylmorpholine → HCID 70564704, compound

HRID 1427300Notes

Reaction equation

HRID 1427300 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-38fde5be228344ebbc327361ecbaf0c3
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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