HCID 70563112, compound → HCID 70564276, compound

HRID 1427301Notes

Reaction equation

HRID 1427301 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:17]2[C:25]3[C:20](=[C:21]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:22]=[CH:23][CH:24]=3)[CH:19]=[N:18]2)([CH2:15][CH3:16])[CH2:9][CH2:10][C:11]([O:13]C)=O)=[CH:4][CH:3]=1.[CH3:31][Li]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:17]2[C:25]3[C:20](=[C:21]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])[CH:22]=[CH:23][CH:24]=3)[CH:19]=[N:18]2)([CH2:9][CH2:10][C:11](=[O:13])[CH3:31])[CH2:15][CH3:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70563112HCID 70563112, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 70564276HCID 70564276, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-(4-chlorophenyl)-4-(4-(methylsulfonamido)-1H-indazol-1-yl)hexanoate (50 mg), as described in Example 44 Step E, in 2 mL of anhydrous THF was added CH3Li (1.5 M in ether, 0.2 mL) dropwise at 0° C. and stirred for 30 min. The solution was quenched with saturated NH4Cl solution, and extracted with ethyl acetate (20 mL). The organic layer was washed with brine, dried over dry sodium sulfate, filtered and evaporated. The residue was purified on revered—phase HPLC (0.05% TFA in H2O-MeCN) to give the title product as a white solid. LC/MS m/z=434.1 [M+H]+.

Workup

  1. customThe solution was quenched with saturated NH4Cl solution
  2. extractionextracted with ethyl acetate (20 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 on revered—phase HPLC (0.05% TFA in H2O-MeCN)

Sources & evidence

ORD record
ord-0758c0e70e17428cb5e2e1084a5d94d0
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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