Water → HCID 178450246, compound

HRID 1797672Notes

Reaction equation

HRID 1797672 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][C:9]1[N:10]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:11](=[O:26])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([C:24]#[N:25])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].Cl.C(N(CC)CC)C.[N-:40]=[N+:41]=[N-:42].[Na+].O>C1(C)C=CC=CC=1>[CH2:20]([O:19][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:24]3[NH:42][N:41]=[N:40][N:25]=3)[CH:16]=2)[C:11](=[O:26])[N:10]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:9]=1[CH2:8][NH:7][C:6](=[O:31])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 22175265HCID 22175265, compound

Product 1

HCID 178450246HCID 178450246, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of tert-butyl(4-butoxy-6-cyano-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.85 g, 2 mmol), triethylamine hydrochloride (0.34 g, 2.5 mmol) and sodium azide (0.16 g, 2.5 mmol) in toluene (20 ml) was stirred at 90° C. for 24 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained crystals were recrystallized from tetrahydrofuran-diisopropyl ether to give tert-butyl [4-butoxy-2-isobutyl-1-oxo-6-(1H-tetrazol-5-yl)-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.50 g, 53.2%) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained crystals were recrystallized from tetrahydrofuran-diisopropyl ether

Sources & evidence

ORD record
ord-6c54b29210514fbf975defe07f8b378c
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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