Sodium Cyanide → HCID 68110058, compound

HRID 1503976Notes

Reaction equation

HRID 1503976 reaction equation
CS(O[CH2:6][CH2:7][C@H:8]1[CH2:19][CH2:18][C:17]2[S:16][C:15]3[N:14]=[CH:13][N:12]=[C:11]([O:20][CH:21]4[CH2:26][CH2:25][CH:24]([N:27]([CH3:36])[CH2:28][C:29](=[O:35])[N:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)[CH2:23][CH2:22]4)[C:10]=3[C:9]1=2)(=O)=O.[C-:37]#[N:38].[Na+]>CS(C)=O.CN(C)C1C=CN=CC=1>[CH3:36][N:27]([CH2:28][C:29](=[O:35])[N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)[CH:24]1[CH2:23][CH2:22][CH:21]([O:20][C:11]2[C:10]3[C:9]4[C@@H:8]([CH2:7][CH2:6][C:37]#[N:38])[CH2:19][CH2:18][C:17]=4[S:16][C:15]=3[N:14]=[CH:13][N:12]=2)[CH2:26][CH2:25]1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 86695138HCID 86695138, compound

Product 1

HCID 68110058HCID 68110058, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-[(3R)-12-[(4-[methyl[2-oxo-2-(pyrrolidin-1-yl)ethyl]amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]ethyl methanesulfonate (107 mg, 0.20 mmol, 1.00 equiv) in DMSO (5 mL) were added NaCN (58.8 mg, 1.20 mmol, 6.00 equiv) and 4-dimethylaminopyridine (2.4 mg, 0.02 mmol, 0.10 equiv) at room temperature. The resulting solution was stirred for 2 h at 80° C. After cooling to room temperature, the reaction was then quenched by the addition of aqueous FeSO4 solution and extracted with DCM. The organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with DCM/MeOH (10:1) to give the desired 3-[(3S)-12-[(4-[methyl[2-oxo-2-(pyrrolidin-1-yl)ethyl]amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]propanenitrile (80 mg, 86%) as a yellow solid. MS (ES): m/z 468 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction was then quenched by the addition of aqueous FeSO4 solution
  3. extractionextracted with DCM
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b41c24d0a46647e7a2ce4a93a0b032a6
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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