Sodium Cyanide → HCID 86695213, compound

HRID 1504056Notes

Reaction equation

HRID 1504056 reaction equation
CS(O[CH2:6][C@H:7]1[CH2:18][CH2:17][C:16]2[S:15][C:14]3[C:9](=[C:10]([O:19][CH:20]4[CH2:25][CH2:24][CH:23]([N:26]5[CH2:32][C:28]6([CH2:31][O:30][CH2:29]6)[CH2:27]5)[CH2:22][CH2:21]4)[N:11]=[CH:12][N:13]=3)[C:8]1=2)(=O)=O.[C-:33]#[N:34].[Na+]>CS(C)=O>[CH2:31]1[C:28]2([CH2:27][N:26]([CH:23]3[CH2:24][CH2:25][CH:20]([O:19][C:10]4[N:11]=[CH:12][N:13]=[C:14]5[C:9]=4[C:8]4[C@@H:7]([CH2:6][C:33]#[N:34])[CH2:18][CH2:17][C:16]=4[S:15]5)[CH2:21][CH2:22]3)[CH2:32]2)[CH2:29][O:30]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 86695212HCID 86695212, compound

Product 1

HCID 86695213HCID 86695213, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of [(3S)-12-[(4-[2-oxa-6-azaspiro[3.3]heptan-6-yl]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]methyl methanesulfonate (250 mg, 0.52 mmol, 1.00 equiv) and NaCN (153 mg, 3.12 mmol, 5.99 equiv) in DMSO (10 mL) was stirred for 3 h at 60° C. After cooling, the reaction was quenched by the addition of 30 mL of saturated aqueous sodium bicarbonate and extracted with 3×50 mL of ethyl acetate. The combined organic layers combined were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (10:1) to give 2-[(3R)-12-[(4-[2-oxa-6-azaspiro[3.3]heptan-6-yl]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]acetonitrile (140 mg, 65%) as a colorless oil.

Workup

  1. temperatureAfter cooling
  2. customthe reaction was quenched by the addition of 30 mL of saturated aqueous sodium bicarbonate
  3. extractionextracted with 3×50 mL of ethyl acetate
  4. washThe combined organic layers combined were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2562891b50e8444fa74e9e79c2797c41
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

Loading…