Hydrochloric Acid → HCID 118060486, compound

HRID 2274827Notes

Reaction equation

HRID 2274827 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH:12]=[N:13][N:14]([CH:16]4[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]4)[CH:15]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.Cl>O1CCOCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH:12]=[N:13][N:14]([CH:16]4[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)[CH:15]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118060259HCID 118060259, compound2×

Product 1

HCID 118060486HCID 118060486, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-(4-(6-fluoro-1H-indol-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (Intermediate 16B; 230 mg; 0.60 mmol) in dioxane (3 mL) was added conc. aqueous HCl (3 mL; 36%). The reaction mixture was stirred for 0.5 hour and concentrated to dryness, neutralized with saturated aqueous NaHCO3 (50 mL), extracted with EtOAc (50 ml×2). The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated. The residue was purified by preparative TLC (DCM/MeOH=10/1) to afford 70 mg (41%) of the title compound as a yellow solid.

Workup

  1. concentrationconcentrated to dryness
  2. extractionextracted with EtOAc (50 ml×2)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC (DCM/MeOH=10/1)

Sources & evidence

ORD record
ord-3cdeabc1a5744a558d9e0b144ea8caf7
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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