Hydrochloric Acid → HCID 67959648, compound

HRID 1529365Notes

Reaction equation

HRID 1529365 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[C:12]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25]C)=[O:24])[CH:21]=4)[NH:16][CH:15]=3)[CH:11]=[N:10][CH:9]=2)[CH2:4][CH2:3]1.[OH-].[Na+].Cl>C1COCC1>[NH2:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]2[N:13]=[C:12]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:23]([OH:25])=[O:24])[CH:21]=4)[NH:16][CH:15]=3)[CH:11]=[N:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67959784HCID 67959784, compound

Product 1

HCID 67959648HCID 67959648, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To mixture of methyl 3-(6-(4-aminopiperidin-1-yl)pyrazin-2-yl)-1H-indole-5-carboxylate (236) (60 mg, 0.17 mmol) in THF (1 mL) was added 10% NaOH solution (1 mL). The reaction mixture was heated at 60° C. for 24 h and cooled to 0° C. 1N HCl solution was added to the mixture to attain pH7. The resulting mixture was stirred at RT for 2 h. The resulting precipitate was collected by filtration, washed with water and dried under vacuum to obtain the title compound (30 mg, 57%). MS (ESI, pos. ion) m/z: 337.9 (M+1).

Workup

  1. temperaturecooled to 0° C
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-5befb42e635a4d81b93b6c6fbe373c23
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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