Sodium Cyanide → HCID 178511275, compound

HRID 711956Notes

Reaction equation

HRID 711956 reaction equation
CS(O[C@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13]2[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][N:16]=[C:15]3[CH:22]=[CH:23][S:24][C:14]=23)[CH2:8][CH2:7]1)(=O)=O.[C-:25]#[N:26].[Na+]>CS(C)=O>[N+:19]([C:18]1[C:13]([NH:12][C@@H:9]2[CH2:10][CH2:11][C@H:6]([C:25]#[N:26])[CH2:7][CH2:8]2)=[C:14]2[S:24][CH:23]=[CH:22][C:15]2=[N:16][CH:17]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 178505325HCID 178505325, compound

Product 1

HCID 178511275HCID 178511275, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of trans-4-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl methanesulfonate (0.12 g, 0.32 mmol) and sodium cyanide (0.061 g, 1.2 mmol) in dimethyl sulfoxide (1 mL) was stirred at 90° C. for 6 h. After dilution with EtOAc, the resulting mixture was washed with sat. NaHCO3 solution, water and brine, and then concentrated. The residue was purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane) to give the desired product (32 mg). LCMS calculated for C14H15N4O2S (M+H)+: m/z=303.1. Found: 303.0.

Workup

  1. washAfter dilution with EtOAc, the resulting mixture was washed with sat. NaHCO3 solution, water and brine
  2. concentrationconcentrated
  3. customThe residue was purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-a3f7fad6cc1642299c909be326694ffb
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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