9-Bromo-2-(2-isopropyl-5-methoxymethyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene → 2-(1-isopropyl-3-(methoxymethyl)-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

HRID 1629355Notes

Reaction equation

HRID 1629355 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][N:11]3[C:7](=[N:8][C:9]([C:15]4[N:16]([CH:23]([CH3:25])[CH3:24])[N:17]=[C:18]([CH2:20][O:21][CH3:22])[N:19]=4)=[CH:10]3)[C:6]=2[CH:26]=1>C(Cl)Cl>[CH:23]([N:16]1[C:15]([C:9]2[N:8]=[C:7]3[C:6]4[CH:26]=[CH:2][CH:3]=[CH:4][C:5]=4[O:14][CH2:13][CH2:12][N:11]3[CH:10]=2)=[N:19][C:18]([CH2:20][O:21][CH3:22])=[N:17]1)([CH3:25])[CH3:24]

Participants

3

Reactant 1

HCID 582044449-Bromo-2-(2-isopropyl-5-methoxymethyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene

Product 1

HCID 582044472-(1-isopropyl-3-(methoxymethyl)-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepineYield 107.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 9-bromo-2-(2-isopropyl-5-methoxymethyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene (0.85 g, 2.0 mmol) in IMS (20 mL) was added DCM (6 mL). The mixture was degassed with nitrogen before being treated with palladium on carbon (10% palladium, 50% water, 350 mg). The vessel was evacuated and refilled with hydrogen and stirred at RT18 h before further catalyst was added and the reaction stirred for 72 h. The reaction was filtered then concentrated in vacuo to give 309 as a pale yellow solid (0.73 g, quantitative yield). LCMS RT=4.55 min, [M+H]+=340. 1H NMR 400 MHz (DMSO-d6) δ: 8.37 (2 H, dd, J=9.88, 1.75 Hz), 7.30 (1 H, ddd, J=7.93, 7.18, 1.70 Hz), 7.12-7.12 (1 H, m), 7.03 (1 H, dd, J=8.19, 1.22 Hz), 5.83-5.74 (1 H, m), 4.48-4.47 (4 H, m), 4.36 (2 H, s), 3.28 (3 H, s), 1.45 (6 H, d, J=6.60 Hz)

Workup

  1. customThe mixture was degassed with nitrogen
  2. additionbefore being treated with palladium on carbon (10% palladium, 50% water, 350 mg)
  3. customThe vessel was evacuated
  4. additionrefilled with hydrogen
  5. additionwas added
  6. stirringthe reaction stirred for 72 h
  7. filtrationThe reaction was filtered
  8. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-789fb16b3bc04dca84d8477af0242e1f
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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