Sodium Azide → HCID 86717569, compound

HRID 712117Notes

Reaction equation

HRID 712117 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([N:19]3[C:23]4=[C:24]5[S:30][CH:29]=[CH:28][C:25]5=[N:26][CH:27]=[C:22]4[N:21]=[C:20]3[C@H:31]([OH:33])[CH3:32])[CH2:15][O:14]2)(=O)=O)=CC=1.[N-:34]=[N+:35]=[N-:36].[Na+]>CN(C=O)C.CO>[N:34]([CH2:12][C@@H:13]1[O:14][CH2:15][C@@H:16]([N:19]2[C:23]3=[C:24]4[S:30][CH:29]=[CH:28][C:25]4=[N:26][CH:27]=[C:22]3[N:21]=[C:20]2[C@H:31]([OH:33])[CH3:32])[CH2:17][CH2:18]1)=[N+:35]=[N-:36]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86717465HCID 86717465, compound

Product 1

HCID 86717569HCID 86717569, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ((2R,5S)-5-{2-[(1R)-1-hydroxyethyl]-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-1-yl}tetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate (25 mg, 0.052 mmol) and sodium azide (5.0 mg, 0.077 mmol) in DMF (0.5 mL) was stirred at 60° C. overnight. After cooling to room temperature, the mixture was diluted with methanol and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give desired product (12 mg, 65%). LCMS calculated for C16H19N6O2S (M+H)+: m/z=359.1. Found: 359.0.

Workup

  1. temperatureAfter cooling to room temperature
  2. custompurified with prep-LCMS (XBridge C18 column
  3. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-d1d71c70f8b349ef807f3932bf77e2ab
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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