2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-9-vinyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine → 9-ethyl-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

HRID 886503Notes

Reaction equation

HRID 886503 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[CH:19][C:20]([CH:22]=[CH2:23])=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:24]=2)=[N:7][C:6]([CH3:25])=[N:5]1)([CH3:3])[CH3:2]>C(O)C>[CH2:22]([C:20]1[CH:19]=[CH:18][C:17]2[C:11]3[N:12]([CH:24]=[C:9]([C:8]4[N:4]([CH:1]([CH3:2])[CH3:3])[N:5]=[C:6]([CH3:25])[N:7]=4)[N:10]=3)[CH2:13][CH2:14][O:15][C:16]=2[CH:21]=1)[CH3:23]

Participants

3

Reactant 1

HCID 582046742-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-9-vinyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

Product 1

HCID 582049249-ethyl-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepineYield 62.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-9-vinyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine from Example 447 (0.300 g, 0.894 mmol) was dissolved in ethanol (5 mL) and purged with N2. 10% Palladium on Carbon (0.1:0.9, Palladium:carbon black, 0.0952 g) was added. The resulting suspension was placed under vacuum followed by addition of H2 at atm pressure. This process was repeated three times to saturate the catalyst. The reaction was stirred for 18 hours at room temperature. The reaction mixture was filtered and concentrated to dryness. The crude product was purified using reverse phase chromatography to give 499 (0.189 g, 62.9% yield).

Workup

  1. custompurged with N2
  2. addition10% Palladium on Carbon (0.1:0.9, Palladium:carbon black, 0.0952 g) was added
  3. additionfollowed by addition of H2 at atm pressure
  4. concentrationto saturate the catalyst
  5. filtrationThe reaction mixture was filtered
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-0c6f4bae27ed4bae83fdd1b0ebeba624
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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