Sodium Azide → (S)-2-tert-butoxy-2-(6-(4-chlorophenyl)-8-methyltetrazolo[1,5-a]quinolin-7-yl)ethyl pivalate

HRID 931806Notes

Reaction equation

[C:1]([O:7][CH2:8][C@@H:9]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[C:10]1[C:11]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:13]2)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[N-:41]=[N+:42]=[N-:43].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:7][CH2:8][C@@H:9]([O:36][C:37]([CH3:39])([CH3:40])[CH3:38])[C:10]1[C:11]([C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]1[N:41]=[N:42][N:43]=[C:15]1[CH:14]=[CH:13]2)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 90 °C

Procedure

The mixture of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate (compound of Example 26)(30 mg) and sodium azide (32 mg) in DMF (1 mL) was heated at 90° C. for 4 hours. The mixture was diluted with ethyl acetate, and washed with water and brine, and dried with sodium sulfate. Concentration and purification by flash column chromatography (hexanes/EtOAc) gave (S)-2-tert-butoxy-2-(6-(4-chlorophenyl)-8-methyltetrazolo[1,5-a]quinolin-7-yl)ethyl pivalate (5.9 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C27H32ClN4O3: 495.2. Found: 495.2.

Workup

washwashed with water and brine
dry with materialdried with sodium sulfate
concentrationConcentration and purification by flash column chromatography (hexanes/EtOAc)

Sources & evidence

ORD record: ord-fe9b25fa661b446d8a1055109e13f3c9
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

Loading…