Water → HCID 58392372, compound

HRID 561620Notes

Reaction equation

HRID 561620 reaction equation
[C-:1]#[N:2].[K+].CS(O[CH2:9][CH2:10][C:11]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)([C:14]1[C:22]2[C:17](=[C:18]([CH2:23][S:24][CH3:25])[CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[CH2:12][CH3:13])(=O)=O.O.ClCCl>CS(C)=O>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([C:11]([C:14]2[C:22]3[C:17](=[C:18]([CH2:23][S:24][CH3:25])[CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)([CH2:12][CH3:13])[CH2:10][CH2:9][C:1]#[N:2])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 9032Potassium CyanideHCID 58392474HCID 58392474, compound

Product 1

HCID 58392372HCID 58392372, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

223 mg (3.43 mmol) of potassium cyanide were added to 775 mg (1.71 mmol) of the compound from Example 115A in 12 ml of DMSO. The mixture was stirred at 80° C. for 12 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). 551 mg (84% 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. custom551 mg (84% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-7bbb7706959a46bb9012feefb9c57fd9
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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