N-Propyl-Methyl Piperidinium Bis(trifluoroMethylsulfonyl)Imide → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(1-(trifluoromethyl)-1H-indazol-5-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate

HRID 879351

Reaction equation

HRID 879351 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[CH:15]=[C:14]([C:16]4[S:17][C:18]5[C:24]([C:25]6[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=6)=[C:23]([C@H:32]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:22]([CH3:43])=[CH:21][C:19]=5[N:20]=4)[CH:13]=[CH:12][N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[F:44][C:45]([F:58])([F:57])I1C2C=CC=CC=2C(C)(C)O1.[N-](S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O>C(=S)=S>[C:39]([O:38][C@@H:32]([C:23]1[C:22]([CH3:43])=[CH:21][C:19]2[N:20]=[C:16]([C:14]3[CH:13]=[CH:12][N:11]=[C:10]([C:6]4[CH:5]=[C:4]5[C:9](=[CH:8][CH:7]=4)[N:1]([C:45]([F:58])([F:57])[F:44])[N:2]=[CH:3]5)[CH:15]=3)[S:17][C:18]=2[C:24]=1[C:25]1[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=1)[C:33]([O:35][CH2:36][CH3:37])=[O:34])([CH3:42])([CH3:41])[CH3:40]

Participants

5

Reactant 3

HCID 4176748N-Propyl-Methyl Piperidinium Bis(trifluoroMethylsulfonyl)ImideHCID 160435723,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxoleHCID 86700148HCID 86700148, compound

Product 1

HCID 86700151(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(1-(trifluoromethyl)-1H-indazol-5-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of (S)-ethyl 2-(2-(2-(1H-indazol-5-yl)pyridin-4-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (40 mg, 0.065 mmol) in CS2 (1.5 mL), was added 1-Trifluoromethyl-3,3-dimethyl-1,2-benziodoxole (64 mg, 0.195 mmol), bis(trifluoromethane)sulfonimide (27 mg, 0.0975 mmol). The reaction mixture was heated at 60° C. in sealed microwave vial for 1d. The reaction mixture was washed by saturated NaHCO3, extracted by EtOAc, the organic phase was dried over MgSO4, filtered, concentrated down, purified by silica gel column, eluting by 0-50% EtOAc in hexanes to give the product. LCMS-ESI+: calc'd for C35H30ClF3N4O3S: 679.2 (M+H+); found: 679.2.

Workup

  1. washThe reaction mixture was washed by saturated NaHCO3
  2. extractionextracted by EtOAc
  3. dry with materialthe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated down
  6. custompurified by silica gel column
  7. washeluting by 0-50% EtOAc in hexanes
  8. customto give the product

Sources & evidence

ORD record
ord-290f9bc16bda4745ad44641c63c11cbe
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Linked notes

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