Water → tert-butyl {[2-isobutyl-4-(4-methylphenyl)-6-(2H-tetrazol-5-ylmethoxy)quinolin-3-yl]methyl}carbamate

HRID 1986463Notes

Reaction equation

[C:1]([CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:9]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:8]2[C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)#[N:2].[N-:35]=[N+:36]=[N-:37].[Na+].[Cl-].[NH4+].O>CS(C)=O>[CH2:15]([C:10]1[C:9]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:8]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[C:7]2[C:12](=[CH:13][CH:14]=[C:5]([O:4][CH2:3][C:1]3[N:35]=[N:36][NH:37][N:2]=3)[CH:6]=2)[N:11]=1)[CH:16]([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of tert-butyl {[6-(cyanomethoxy)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate (0.46 g, 1.0 mmol) and sodium azide (0.13 g, 2.0 mmol) in dimethyl sulfoxide (10 ml) was added ammonium chloride (0.22 g, 4.0 mmol), and the mixture was stirred at 70° C. for 24 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from diisopropyl ether to give tert-butyl {[2-isobutyl-4-(4-methylphenyl)-6-(2H-tetrazol-5-ylmethoxy)quinolin-3-yl]methyl}carbamate (0.47 g, yield 93%) as pale-yellow crystals.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record: ord-fe62a243238c47f895d5c5eab76d6c0d
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547710B2

Reaction notes

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