Hydrazine hydrate (1:1) → HCID 22176261, compound

HRID 1797754Notes

Reaction equation

HRID 1797754 reaction equation
[C:1]([O:5][C:6](=[O:42])[NH:7][CH2:8][C:9]1[N:10]([CH2:38][CH:39]([CH3:41])[CH3:40])[C:11](=[O:37])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([CH2:25][N:26]1C(=O)C3C(=CC=CC=3)C1=O)=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)C.O1CCCC1>[C:1]([O:5][C:6](=[O:42])[NH:7][CH2:8][C:9]1[N:10]([CH2:38][CH:39]([CH3:40])[CH3:41])[C:11](=[O:37])[C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:16][C:15]([CH2:25][NH2:26])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22176142HCID 22176142, compound

Product 1

HCID 22176261HCID 22176261, compoundYield 125.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl{6-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl}methylcarbamate (0.85 g, 1.5 mmol), and hydrazine monohydrate (0.6 mL, 12 mmol) in ethanol (20 mL) and tetrahydrofuran (10 mL) was stirred at room temperature for 17 h. The reaction mixture was filtered, and the filtrate was concentrated. After the residue was dissolved in ethyl acetate (50 mL), the solution was filtrated to remove insoluble material. The filtrate was concentrated to give tert-butyl[6-(aminomethyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.82 g) as a crude pale yellow oil. To a solution of the crude oil (0.16 g) in tetrahydrofuran (2 mL) was added acetic anhydride (0.034 mL, 0.36 mmol), and then the mixture was stirred at room temperature for 4 h. The reaction mixture was washed with water (4 mL) and concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1 (v/v)) to give tert-butyl{6-[(acetylamino)methyl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.090 g, 63%) as a pale yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionAfter the residue was dissolved in ethyl acetate (50 mL)
  4. filtrationthe solution was filtrated
  5. customto remove insoluble material
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-be84cb9142d74e86918b601dbfd8448d
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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