4-Methylmorpholine → N-(1-(3-(4-chlorophenyl)-1,1,1-trifluoropentan-3-yl)-1H-indazol-4-yl)methane sulfonamide

HRID 1477908Notes

Reaction equation

HRID 1477908 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([NH2:25])[C:19]=3[CH:18]=[N:17]2)([CH2:14][CH3:15])[CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:4][CH:3]=1.CN1CCOCC1.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][S:34]([CH3:33])(=[O:36])=[O:35])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17]2)([CH2:14][CH3:15])[CH2:9][C:10]([F:13])([F:11])[F:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 705766821-(3-(4-chlorophenyl)-1,1,1-trifluoropentan-3-yl)-1H-indazol-4-amine

Product 1

HCID 70562836N-(1-(3-(4-chlorophenyl)-1,1,1-trifluoropentan-3-yl)-1H-indazol-4-yl)methane sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of the product of Step F (50 mg, 0.13 mmol) and NMM (31 mg, 0.3 mmol) in DCM (3 mL) was added methanesulfonyl chloride (20 mg, 0.21 mmol). The mixture was stirred at room temperature for 3 h, then quenched with saturated ammonium chloride solution (10 mL), and extracted with ethyl acetate. The organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated. The residue was purified by Pre-HPLC (Mobile phase: acetonitrile/water (0.03% TFA)) to afford the title compound. LC/MS m/z=446.11[M+H]+.

Workup

  1. customquenched with saturated ammonium chloride solution (10 mL)
  2. extractionextracted with ethyl acetate
  3. washThe organic layers were washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by Pre-HPLC (Mobile phase: acetonitrile/water (0.03% TFA))

Sources & evidence

ORD record
ord-8330a02bbfd94413ae23ef22f64ad05a
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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