Sodium Hydroxide → HCID 67090502, compound

HRID 2113534Notes

Reaction equation

HRID 2113534 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), fioltered 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. customsolvent removed at reduced pressure

Sources & evidence

ORD record
ord-1f527716ffe14ba8b9fa5901783a09c8
Source dataset
uspto-grants-2008_10
Patent number
US07432270B2

Reaction notes

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