Bis-(1H-imidazol-2-YL)-methanone → 3-cyclohexyl-N-{1-oxo-6-phenyl-1H,4H-[1,2,4}oxadiazolo[4,3-a][1,4]benzodiazepin-4-yl}propanamide

HRID 1489524Notes

Reaction equation

HRID 1489524 reaction equation
[C:1](C1NC=CN=1)(C1NC=CN=1)=[O:2].[CH:13]1([CH2:19][CH2:20][C:21]([NH:23][CH:24]2[C:25](=[N:41][OH:42])[NH:26][C:27]3[CH:40]=[CH:39][CH:38]=[CH:37][C:28]=3[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[N:30]2)=[O:22])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C1COCC1>[CH:13]1([CH2:19][CH2:20][C:21]([NH:23][CH:24]2[N:30]=[C:29]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:28]3[CH:37]=[CH:38][CH:39]=[CH:40][C:27]=3[N:26]3[C:1](=[O:2])[O:42][N:41]=[C:25]23)=[O:22])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 178520437HCID 178520437, compound

Product 1

HCID 867514163-cyclohexyl-N-{1-oxo-6-phenyl-1H,4H-[1,2,4}oxadiazolo[4,3-a][1,4]benzodiazepin-4-yl}propanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyl diimidazole (35 mg, 0.21 mmol) was added to a solution of (Z)-3-cyclohexyl-N-(2,3-dihydro-2-hydroxyimino-5-phenyl-1H-1,4-benzodiazepin-3-yl)propanamide (80 mg, 0.2 mmol) in THF (15 mL) and the mixture was heated under reflux for 1 h. The solvent was evaporated under reduced pressure and the residue was triturated with ethanol (6 mL). The solid was collected and dried in vacuo to give 3-cyclohexyl-N-{1-oxo-6-phenyl-1H ,4H-[1,2,4}oxadiazolo[4,3-a][1,4]benzodiazepin-4-yl}propanamide as a solid, m.p. 226° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 h
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was triturated with ethanol (6 mL)
  5. customThe solid was collected
  6. customdried in vacuo

Sources & evidence

ORD record
ord-bfe18af28b39434b82d970d79078b85d
Source dataset
uspto-grants-1997_10
Patent number
US05679672

Reaction notes

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