Sodium Hydroxide → HCID 67007881, compound

HRID 2043474Notes

Reaction equation

HRID 2043474 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:20]=[C:19]([NH:21][C:22]3[CH:27]=[N:26][CH:25]=[CH:24][N:23]=3)[CH:18]=[CH:17][C:12]=2[C:13]([O:15]C)=[O:14])[CH3:9])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:20]=[C:19]([NH:21][C:22]3[CH:27]=[N:26][CH:25]=[CH:24][N:23]=3)[CH:18]=[CH:17][C:12]=2[C:13]([OH:15])=[O:14])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 46865920HCID 46865920, compound

Product 1

HCID 67007881HCID 67007881, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.0 g of methyl (S)-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)nicotinate was dissolved in 60 ml of methanol, and 20 ml of 10% sodium hydroxide aqueous solution was added thereto, and the reaction solution was heated at reflux for 4 hour. The reaction solution was distilled off under reduced pressure to remove methanol. The obtained aqueous layer was washed with diethyl ether, and the pH of the mixture was adjusted to 3 by 10% hydrochloric acid. The precipitated solid was filtered, and washed with water. The obtained solid was dried under reduced pressure to obtain 880 mg of the objective compound as pale yellow powder.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureat reflux for 4 hour
  3. distillationThe reaction solution was distilled off under reduced pressure
  4. customto remove methanol
  5. washThe obtained aqueous layer was washed with diethyl ether
  6. filtrationThe precipitated solid was filtered
  7. washwashed with water
  8. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-d305c713d3294d06a053d306961fc246
Source dataset
uspto-grants-2013_11
Patent number
US08586591B2

Reaction notes

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