Hydrochloric Acid → HCID 22175663, compound

HRID 1797605Notes

Reaction equation

HRID 1797605 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][C:9]1[N:10]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:11](=[O:27])[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]([C:25]#[N:26])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].[N-:33]=[N+:34]=[N-:35].[Na+].Cl.C(N(CC)CC)C.Cl>C1(C)C=CC=CC=1.O>[CH2:28]([N:10]1[C:9]([CH2:8][NH:7][C:6](=[O:32])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[C:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:25]3[N:33]=[N:34][NH:35][N:26]=3)[CH:16]=2)[C:11]1=[O:27])[CH:29]([CH3:30])[CH3:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 22175473HCID 22175473, compound

Product 1

HCID 22175663HCID 22175663, compoundYield 37.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution (30 mL) of tert-butyl(6-cyano-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.86 g, 2.0 mmol) in toluene were added sodium azide (0.16 g, 2.5 mmol) and triethylamine hydrochloride (0.28 g, 2.5 mmol) and the mixture was stirred at 90° C. for 24 h. The reaction mixture was poured into water (100 mL), acidified with 1N hydrochloric acid and extracted twice with ethyl acetate (50 mL). The extracts were combined and washed with saturated brine (15 mL), dried over anhydrous magnesium sulfate (12 g) and concentrated under reduced pressure. The residue was recrystallized from tetrahydrofuran-diisopropyl ether (1:5) to give tert-butyl [2-isobutyl-1-oxo-4-phenyl-6-(2H-tetrazol-5-yl)-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.36 g, 37%) as colorless crystals.

Workup

  1. extractionextracted twice with ethyl acetate (50 mL)
  2. washwashed with saturated brine (15 mL)
  3. dry with materialdried over anhydrous magnesium sulfate (12 g)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from tetrahydrofuran-diisopropyl ether (1:5)

Sources & evidence

ORD record
ord-c3ac831183a94d19b4b0f7cf90c34fb7
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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