Water → HCID 86666142, compound

HRID 1039052Notes

Reaction equation

CC1C=CC(S(O[CH2:12][CH2:13][C@@H:14]2[CH2:16][C@@H:15]2[CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[N:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=3)[CH2:19][CH2:18]2)(=O)=O)=CC=1.[N-:30]=[N+:31]=[N-:32].[Na+].O>O1CCOCC1>[N:30]([CH2:12][CH2:13][C@@H:14]1[CH2:16][C@@H:15]1[CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[N:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=2)[CH2:19][CH2:18]1)=[N+:31]=[N-:32]

Participants

Conditions

Temperature: 100 °C

Procedure

2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl 4-methylbenzenesulfonate (65 mg, 0.15 mmol) from step 1 of this example was dissolved in dioxane (1.2mL). Sodium azide (22.3 mg, 0.34 mmol) was added, then water (0.3 mL). The reaction was heated to 100° C. to reflux for 2 hours. The reaction was cooled to room temperature, water (10 mL) was added and extracted with EtOAc (10 mL×2). The combined organic phase was dried by magnesium sulfate, filter, concentrated and purified by column chromatography through a 12 gram RediSep Rf™ silica gel cartridge eluting with 5% ethyl acetate/hexanes to give the title compound as a white solid.

Workup

temperatureto reflux for 2 hours
temperatureThe reaction was cooled to room temperature
extractionextracted with EtOAc (10 mL×2)
dry with materialThe combined organic phase was dried by magnesium sulfate
filtrationfilter
concentrationconcentrated
custompurified by column chromatography through a 12 gram RediSep Rf™ silica gel cartridge
washeluting with 5% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-546dec1f5c8643b0bbe43be38ca9a820
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552022B2

Reaction notes

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