Sodium Cyanide → HCID 86695229, compound

HRID 1504068Notes

Reaction equation

HRID 1504068 reaction equation
CS(O[CH2:6][CH2:7][C@H:8]1[C:20]2[C:19]3[C:18]([O:21][CH:22]4[CH2:27][CH2:26][CH:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:24][CH2:23]4)=[N:17][CH:16]=[N:15][C:14]=3[S:13][C:12]=2[CH2:11][CH2:10][CH2:9]1)(=O)=O.[C-:36]#[N:37].[Na+]>CS(C)=O.C(Cl)Cl>[C:36]([CH2:6][CH2:7][C@H:8]1[C:20]2[C:19]3[C:18]([O:21][CH:22]4[CH2:27][CH2:26][CH:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[CH2:24][CH2:23]4)=[N:17][CH:16]=[N:15][C:14]=3[S:13][C:12]=2[CH2:11][CH2:10][CH2:9]1)#[N:37]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 86695228HCID 86695228, compound

Product 1

HCID 86695229HCID 86695229, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of tert-butyl N-(4-[[(13S)-13-[2-(methanesulfonyloxy)ethyl]-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate (525 mg, 1.00 mmol, 1.00 equiv) in DMSO (20 mL) was added NaCN (294 mg, 6.00 mmol, 6.00 equiv) and the resulting solution was stirred for 2 h at 70° C. under nitrogen. After cooling, the mixture was diluted with DCM (80 mL), 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 (1:3) to yield 380 mg (83%) of tert-butyl N-(4-[[(13S)-13-(2-cyanoethyl)-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate as a white solid.

Workup

  1. temperatureAfter cooling
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f3730c204f0340bdaeefea7dfdc7420b
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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