Hydrochloric Acid → 2-(2-Isopropyl-5-methyl-1,2,4-triazol-3-yl)-9-[2-(3-piperidyl)pyrazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine

HRID 1530673Notes

Reaction equation

HRID 1530673 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]2[C:18]([C:19]3[CH:41]=[CH:40][C:22]4[C:23]5[N:24]([CH:28]=[C:29]([C:31]6[N:35]([CH:36]([CH3:38])[CH3:37])[N:34]=[C:33]([CH3:39])[N:32]=6)[N:30]=5)[CH2:25][CH2:26][O:27][C:21]=4[CH:20]=3)=[CH:17][CH:16]=[N:15]2)[CH2:9]1)C1C=CC=CC=1.Cl.O1CCOCC1>CO.[Pd]>[CH:36]([N:35]1[C:31]([C:29]2[N:30]=[C:23]3[C:22]4[CH:40]=[CH:41][C:19]([C:18]5[N:14]([CH:10]6[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]6)[N:15]=[CH:16][CH:17]=5)=[CH:20][C:21]=4[O:27][CH2:26][CH2:25][N:24]3[CH:28]=2)=[N:32][C:33]([CH3:39])=[N:34]1)([CH3:38])[CH3:37]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 683131799-(1-(1-benzylpiperidin-3-yl)-1H-pyrazol-5-yl)-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

Product 1

HCID 683130012-(2-Isopropyl-5-methyl-1,2,4-triazol-3-yl)-9-[2-(3-piperidyl)pyrazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

9-(1-(1-benzylpiperidin-3-yl)-1H-pyrazol-5-yl)-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (500 mg, 0.0009 mol) was dissolved in Methanol (10 mL). 4.0 M of Hydrogen chloride in 1,4-Dioxane (0.5 mL, 0.002 mol) was added. 10% Palladium on Carbon (0.1:0.9, Palladium: carbon black, 120 mg, 0.00011 mol) was added under a stream of Nitrogen. The reaction mixture was vac/flushed with H2 (balloon) and stirred overnight at room temperature. LCMS show reaction is complete. The reaction mixture was filtered and concentrated to dryness to give 2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-9-(1-(piperidin-3-yl)-1H-pyrazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

Workup

  1. customThe reaction mixture was vac/flushed with H2 (balloon)
  2. customLCMS show reaction
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4f32a797b75a4c4b80fb26212c7c3804
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

Loading…