Flumazenil → Ro 15-3890

HRID 129542Notes

Reaction equation

HRID 129542 reaction equation
CC[O:3][C:4]([C:6]1[N:16]=[CH:15][N:14]2[C:7]=1[CH2:8][N:9]([CH3:22])[C:10]([C:12]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:13]=12)=[O:11])=[O:5]>[OH-].[K+]>[F:21][C:19]1[CH:18]=[CH:17][C:13]2[N:14]3[CH:15]=[N:16][C:6]([C:4]([OH:5])=[O:3])=[C:7]3[CH2:8][N:9]([CH3:22])[C:10](=[O:11])[C:12]=2[CH:20]=1

Participants

3

Reactant 1

HCID 3373Flumazenil

Product 1

HCID 134757Ro 15-3890Yield 97%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Ro 15-1788 (0.82 g, 2.71 mmol) was dissolved in 80 ml of 10% methanolic KOH and the solution was stirred for 24 h at room temperature. The solvent was evaporated in vacuo and the residue was dissolved in 50 ml of distilled water. The aqueous solution was cooled to 4° C. and the pH adjusted to 6 by dropwise addition of 1M aqueous HCl. The desired product was crystallized from the solution at pH 6. The solution was left to stand at 4° C. for 10 min and filtered. The filter cake was washed with ice-cold distilled water and dried overnight in vacuo at 60° C. to give III (0.72 g, 97%); crystallization from 50% aqueous ethanol (20 ml) afforded small colorless laminae: mp 273°-274° C.; 1H-NMR (d6 -DMSO) δ 3.08 (s, 3H, NMe), 4.60 (m, 1H), 5.05 (m, 1H), 7.60-7.67 (m, 2H), 7.79 (dd, 1H, J=4.5 Hz, J=8.50 Hz), 8.29 (s, 1H); IR (KBr) 2000-3600, 3110, 1700 (broad), 1670, 1490, 1220, 890 cm-1 ; CIMS M+H=276, C13H10FN3O23 requires M+H=276. Analysis calculated for C213H10FN3O3 :C 56.73, H 3.66, and N 15.27% showed C 56.80, H 3.71, and N 15.29%.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in 50 ml of distilled water
  3. temperatureThe aqueous solution was cooled to 4° C.
  4. additionthe pH adjusted to 6 by dropwise addition of 1M aqueous HCl
  5. customThe desired product was crystallized from the solution at pH 6
  6. waitThe solution was left
  7. waitto stand at 4° C. for 10 min
  8. filtrationfiltered
  9. washThe filter cake was washed with ice-cold
  10. distillationdistilled water
  11. customdried overnight in vacuo at 60° C.

Sources & evidence

ORD record
ord-253b1cb6da524ef5aa5c4428db4eb3d1
Source dataset
uspto-grants-1995_11
Patent number
US05468854

Reaction notes

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