Hydrochloric Acid → (S)-ethyl 2-(2-(2-(1-(azetidin-3-yl)-1H-indazol-5-yl)pyridin-4-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

HRID 879353Notes

Reaction equation

HRID 879353 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:46]([CH3:47])=[CH:45][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:26]=[C:27]5[C:31](=[CH:32][CH:33]=4)[N:30]([CH:34]4[CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35]4)[N:29]=[CH:28]5)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:48]1[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].Cl.CCOC(C)=O>C(O)(C)C.O1CCOCC1>[NH:36]1[CH2:37][CH:34]([N:30]2[C:31]3[C:27](=[CH:26][C:25]([C:21]4[CH:20]=[C:19]([C:17]5[S:18][C:14]6[C:13]([C:48]7[CH:49]=[CH:50][C:51]([Cl:54])=[CH:52][CH:53]=7)=[C:12]([C@H:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:46]([CH3:47])=[CH:45][C:15]=6[N:16]=5)[CH:24]=[CH:23][N:22]=4)=[CH:33][CH:32]=3)[CH:28]=[N:29]2)[CH2:35]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86700152(S)-tert-butyl 3-(5-(4-(6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)pyridin-2-yl)-1H-indazol-1-yl)azetidine-1-carboxylate

Product 1

HCID 86700153(S)-ethyl 2-(2-(2-(1-(azetidin-3-yl)-1H-indazol-5-yl)pyridin-4-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-tert-butyl 3-(5-(4-(6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)pyridin-2-yl)-1H-indazol-1-yl)azetidine-1-carboxylate (54 mg, 0.070 mmol) in isopropanol (3 mL) was added HCl in Dioxane (3 mL, 4 N in dioxane). The reaction mixture was stirred at room temperature. After the reaction finished, the reaction mixture was diluted by EtOAc, washed by saturated NaHCO3, back-extracted by EtOAc, the organic phase was dried over MgSO4, filtered, concentrated down, purified by silica gel column, eluting by 0-100% EtOAc in hexanes to give the product. LCMS-ESI+: calc'd for C37H36ClN5O3S: 666.2 (M+H+); found: 666.3.

Workup

  1. washwashed by saturated NaHCO3
  2. extractionback-extracted 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 0-100% EtOAc in hexanes
  8. customto give the product

Sources & evidence

ORD record
ord-8089ccc9b7b74543a63e8f8446a187dd
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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