Sodium Azide → HCID 178445666, compound

HRID 2368163Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-{trans-4-[6-(cyclopropylmethoxy)-2H-indazol-2-yl]cyclohexyl}-1-methylpropyl methanesulfonate (2.95 g), sodium azide (1.37 g) and DMF (100 mL) was stirred at 80° C. for 2 hr. The reaction mixture was allowed to cool to room temperature, and concentrated under reduced pressure. The residue was diluted with ethyl acetate and water, and the organic layer was separated. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (2.50 g).

Workup

temperatureto cool to room temperature
concentrationconcentrated under reduced pressure
additionThe residue was diluted with ethyl acetate and water
customthe organic layer was separated
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-88fe2b8ba39940b5886187b09a45063b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703758B2

Reaction notes

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