Tetrahydrofuran → HCID 22175381, compound

HRID 1797758Notes

Reaction equation

HRID 1797758 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3](OCC)=O.[OH2:10].[NH2:11][NH2:12].[C:13](O)(=O)C.C(O)(=O)C.C([N:25]([CH2:29][C:30]1[N:31]([CH2:50][CH:51]([CH3:53])[CH3:52])[C:32](=O)[C:33]2[C:38]([C:39]=1[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[CH:37][C:36]([C:46](N)=[NH:47])=[CH:35][CH:34]=2)[C:26](=O)[OH:27])(C)(C)C.[OH-:54].[Na+].O1[CH2:60][CH2:59][CH2:58]C1>>[C:59]([O:10][C:26](=[O:27])[NH:25][CH2:29][C:30]1[N:31]([CH2:50][CH:51]([CH3:53])[CH3:52])[C:32](=[O:54])[C:33]2[C:38]([C:39]=1[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[CH:37][C:36]([C:46]1[N:47]=[C:3]([C:2]([F:1])([F:8])[F:9])[NH:12][N:11]=1)=[CH:35][CH:34]=2)([CH3:58])([CH3:60])[CH3:13]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 9794Ethyl trifluoroacetateHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 86760035HCID 86760035, compound

Product 1

HCID 22175381HCID 22175381, compoundYield 55%

Procedure

A mixture of ethyl trifluoroacetate (0.038 mL, 0.31 mmol) and hydrazine monohydrate (0.026 mL, 0.50 mmol) in tetrahydrofuran (3 mL) was refluxed in a sealed tube for 1 h, the reaction was allowed to cool to room temperature. To the mixture were added tert-butyl{6-[amino(imino)methyl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl}methylcarbamate diacetate (0.14 g, 0.25 mmol) and sodium hydroxide (0.027 g, 0.55 mmol), and the resulting mixture was refluxed for 3 h. The reaction mixture was partitioned between water (10 mL) and ethyl acetate (30 mL). The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel-column chromatography (n-hexane:ethyl acetate=3:1 (v/v)) to give tert-butyl{2-isobutyl-1-oxo-4-phenyl-6-[5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl]-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.074 g, 55%) as a colorless powder.

Workup

  1. temperaturewas refluxed in a sealed tube for 1 h
  2. temperaturethe resulting mixture was refluxed for 3 h
  3. customThe reaction mixture was partitioned between water (10 mL) and ethyl acetate (30 mL)
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel-column chromatography (n-hexane:ethyl acetate=3:1 (v/v))

Sources & evidence

ORD record
ord-764959f0ec774e4e9f18b53281654abd
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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