HCID 59600663, compound → HCID 59600665, compound

HRID 2267500Notes

Reaction equation

HRID 2267500 reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[CH:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1)=[O:3]>CO.Cl.O1CCOCC1>[F:32][C:29]1[CH:28]=[CH:27][C:26]([C:6]2[CH:7]=[C:8]3[C:12](=[C:4]([C:2]([NH2:1])=[O:3])[CH:5]=2)[NH:11][CH:10]=[C:9]3[CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:31][CH:30]=1

Participants

5

Reactant 1

HCID 59600663HCID 59600663, compound

Product 1

HCID 59600665HCID 59600665, compoundYield 80.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-[7-(aminocarbonyl)-5-(4-fluorophenyl)-1H-indol-3-yl]-1-piperidinecarboxylate (92.9 g, 0.205 mmol) in methanol (10 mL), HCl in dioxane (4M, 2.01 mL) was added. The reaction mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure and the resulting residue was partitioned between ethyl acetate (50 mL) and 5% of aqueous NaOH (50 mL). The aqueous layer washed with ethyl acetate (2×50 mL) and the combined organic phases were dried and concentrated under reduced pressure to give desired product (55.9 mg, 78%), which was used in the next step without further purification.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe resulting residue was partitioned between ethyl acetate (50 mL) and 5% of aqueous NaOH (50 mL)
  3. washThe aqueous layer washed with ethyl acetate (2×50 mL)
  4. customthe combined organic phases were dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dd4e6ca6837248b9b7670fd1d46d7cbb
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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