HCID 67050705, compound → HCID 67050715, compound

HRID 1498503Notes

Reaction equation

HRID 1498503 reaction equation
[CH3:1][O:2][C:3](=[O:29])/[C:4](/[CH3:28])=[CH:5]/[C:6]1[CH:27]=[CH:26][C:9]2[C:10]3[N:14]([CH2:15][CH2:16][O:17][C:8]=2[CH:7]=1)[CH:13]=[C:12]([C:18]1[N:19]([CH:23]([CH3:25])[CH3:24])[N:20]=[CH:21][N:22]=1)[N:11]=3>[Pd]>[CH3:1][O:2][C:3](=[O:29])[CH:4]([CH3:28])[CH2:5][C:6]1[CH:27]=[CH:26][C:9]2[C:10]3[N:14]([CH2:15][CH2:16][O:17][C:8]=2[CH:7]=1)[CH:13]=[C:12]([C:18]1[N:19]([CH:23]([CH3:24])[CH3:25])[N:20]=[CH:21][N:22]=1)[N:11]=3

Participants

3

Reactant 1

HCID 67050705HCID 67050705, compound

Product 1

HCID 67050715HCID 67050715, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

To a solution of (E)-3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yl]-2-methyl-acrylic acid methyl ester (181 mg, 0.46 mmol) in IMS (10 mL) was added palladium on carbon (200 mg, 10%). The reaction was stirred at RT under an atmosphere of hydrogen for 16 h. More palladium on carbon (200 mg, 10%) was added and the reaction stirred at RT under an atmosphere of hydrogen for a further 16 h. The reaction mixture was filtered and the filtrate concentrated in vacuo to give 3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yl]-2-methyl-propionic acid methyl ester as a yellow oil (150 mg, 82%). LCMS: RT=3.40 min, [M+H]+=396.

Workup

  1. stirringthe reaction stirred at RT under an atmosphere of hydrogen for a further 16 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-6a4ef8b61e914378ada0efde37e91f40
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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