Sodium Hydroxide → HCID 67090502, compound

HRID 2074403Notes

Reaction equation

HRID 2074403 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[CH2:18][NH:19][C:20]2[CH:29]=[N:28][C:27]3[C:22](=[CH:23][C:24]([F:31])=[C:25]([F:30])[CH:26]=3)[N:21]=2)=[O:11])[CH:5]=1.[OH-].[Na+]>CO.O>[F:30][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[F:31])[N:21]=[C:20]([NH:19][CH2:18][C@@H:13]1[CH2:14][CH2:15][CH2:16][CH2:17][N:12]1[C:10]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:32])=[O:2])=[O:11])[CH:29]=[N:28]2

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 67090301HCID 67090301, compound

Product 1

HCID 67090502HCID 67090502, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-(1-{(S)-2-[(6,7-Difluoro-quinoxalin-2-ylamino)-methyl]-piperidin-1-yl}-methanoyl)-benzoic acid methyl ester (0.5 g) was dissolved in methanol (15 ml) and treated with 1M sodium hydroxide (1.7 ml). The reaction mixture was stirred for 12 h, additional 1M sodium hydroxide (1.7 ml) added and stirring continued for a further 24 h. The reaction mixture was diluted with water and washed with ethyl acetate. The aqueous phase was acidified with 2M hydrochloric acid and extracted with ethyl acetate (×3). the combined organic phase was dried (MgSO4), filtered and solvent removed at reduced pressure to give the title compound (0.463 g) as a yellow solid.

Workup

  1. stirringstirring
  2. waitcontinued for a further 24 h
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate (×3)
  5. dry with materialthe combined organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. customsolvent removed at reduced pressure

Sources & evidence

ORD record
ord-27ab4e420c9242e6ac4ba4018bb0af76
Source dataset
uspto-grants-2011_04
Patent number
US07919507B2

Reaction notes

Loading…