Sodium Cyanide → HCID 178511085, compound

HRID 711934Notes

Reaction equation

HRID 711934 reaction equation
CS(O[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][N:17]=[C:16]3[CH:23]=[CH:24][S:25][C:15]=23)[CH2:9][CH2:8]1)(=O)=O.[C-:26]#[N:27].[Na+]>CS(C)=O.CCOC(C)=O>[N+:20]([C:19]1[C:14]([NH:13][C@H:10]2[CH2:11][CH2:12][C@H:7]([CH2:6][C:26]#[N:27])[CH2:8][CH2:9]2)=[C:15]2[S:25][CH:24]=[CH:23][C:16]2=[N:17][CH:18]=1)([O-:22])=[O:21]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 178505298HCID 178505298, compound

Product 1

HCID 178511085HCID 178511085, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of {trans-4-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}methyl methanesulfonate (0.20 g, 0.52 mmol) and sodium cyanide (0.057 g, 1.2 mmol) in dimethyl sulfoxide (2 mL) was stirred at 90° C. for 4 h. After diluting with EtOAc, the resulting mixture was washed with sat. NaHCO3 solution, water and brine, then concentrated. The residue was purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane) to give the desired product. LCMS calculated for C15H17N4O2S (M+H)+: m/z=317.1. Found: 317.0.

Workup

  1. washthe 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-f81e97e8643244b3a248f675651a72a6
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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