Water → HCID 58392179, compound

HRID 561618Notes

Reaction equation

[C-:1]#[N:2].[K+].CS(O[CH2:9][CH2:10][C:11]([C:23]1[C:31]2[C:26](=[C:27]([CH2:32][S:33][CH3:34])[CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)([C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)[CH3:12])(=O)=O.O.ClCCl>CS(C)=O>[CH3:34][S:33][CH2:32][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:26]=1[NH:25][CH:24]=[C:23]2[C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:22])[F:21])=[CH:15][CH:14]=1)([CH3:12])[CH2:10][CH2:9][C:1]#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

33 mg (0.50 mmol) of potassium cyanide were added to 118 mg (0.25 mmol) of the compound from Example 113A in 1.5 ml of DMSO. The mixture was stirred at 80° C. for 4 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). 62 mg (62% of theory) of the target compound were obtained.

Workup

customthe phases were separated
extractionThe organic phase was extracted with dichloromethane
customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)
custom62 mg (62% of theory) of the target compound were obtained

Sources & evidence

ORD record: ord-13056ddd6b664aedb211312d4ab023bc
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

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