Ammonium Chloride → HCID 86605653, compound

HRID 1986481Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of tert-butyl [6-cyano-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methylcarbamate (0.60 g, 1.4 mmol), sodium azide (0.18 g, 2.8 mmol), ammonium chloride (0.30 g, 3.6 mmol) and dimethyl sulfoxide (810 ml) was stirred at 70° C. for 2 days. The reaction mixture was partitioned between ethyl acetate and 0.1N hydrochloric acid. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from n-hexane-ethyl acetate to give tert-butyl [2-isobutyl-4-(4-methylphenyl)-6-(2H-tetrazol-5-yl)quinolin-3-yl]methylcarbamate (0.38 g, yield 57%) as a white powder.

Workup

customThe reaction mixture was partitioned between ethyl acetate and 0.1N hydrochloric acid
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was crystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record: ord-c972ef9c28fa4fa5bcce2d463b5f9216
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547710B2

Reaction notes

Loading…