Water → HCID 58392132, compound

HRID 561619Notes

Reaction equation

HRID 561619 reaction equation
[C-:1]#[N:2].[K+].CS(O[CH2:9][CH2:10][C:11]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)([C:13]1[C:21]2[C:16](=[C:17]([CH2:22][S:23][CH3:24])[CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[CH3:12])(=O)=O.O.ClCCl>CS(C)=O>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([C:11]([C:13]2[C:21]3[C:16](=[C:17]([CH2:22][S:23][CH3:24])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)([CH3:12])[CH2:10][CH2:9][C:1]#[N:2])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 9032Potassium CyanideHCID 58392126HCID 58392126, compound

Product 1

HCID 58392132HCID 58392132, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

128 mg (1.96 mmol) of potassium cyanide were added to 430 mg (0.98 mmol) of the compound from Example 114A in 8 ml of DMSO. The mixture was stirred at 80° C. for 8 h, water and dichloromethane were added to the reaction solution, and the phases were separated. The organic phase was extracted with dichloromethane, and the combined organic phases were freed of solvent. The crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 280 mg (77% of theory) of the target compound were obtained.

Workup

  1. customthe phases were separated
  2. extractionThe organic phase was extracted with dichloromethane
  3. customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)
  4. custom280 mg (77% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-45473293a98e4379a574d7dbe255c866
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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