Sodium Cyanide → HCID 86695148, compound

HRID 1503992Notes

Reaction equation

HRID 1503992 reaction equation
CS(O[CH2:6][C@H:7]1[CH2:18][CH2:17][C:16]2[S:15][C:14]3[N:13]=[CH:12][N:11]=[C:10]([O:19][CH:20]4[CH2:25][CH2:24][CH:23]([N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH2:21]4)[C:9]=3[C:8]1=2)(=O)=O.[C-:35]#[N:36].[Na+]>CS(C)=O.CN(C)C1C=CN=CC=1>[C:35]([CH2:6][C@H:7]1[CH2:18][CH2:17][C:16]2[S:15][C:14]3[N:13]=[CH:12][N:11]=[C:10]([O:19][CH:20]4[CH2:21][CH2:22][CH:23]([N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[CH2:24][CH2:25]4)[C:9]=3[C:8]1=2)#[N:36]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 86695147HCID 86695147, compound

Product 1

HCID 86695148HCID 86695148, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed tert-butyl N-(4-[[(3S)-3-[(methanesulfonyloxy)methyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2 (6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (900 mg, 1.76 mmol, 1.00 equiv) in 6 mL of DMSO at room temperature. NaCN (600 mg, 12.24 mmol, 6.96 equiv) and 4-dimethylaminopyridine (100 mg, 0.82 mmol, 0.47 equiv) were added and the resulting solution was stirred for 2 h at 80° C. After cooling to room temperature, the reaction was quenched with water and extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:4) to provide tert-butyl N-(4-[[(3R)-3-(cyanomethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2 (6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (709 mg, 91%) as a white solid. MS: m/z 443 (M+H)+.

Workup

  1. customInto a 50-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customat room temperature
  4. temperatureAfter cooling to room temperature
  5. customthe reaction was quenched with water
  6. extractionextracted with 3×50 mL of ethyl acetate
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0f8da422b84640d28ec8090b5694e027
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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