Potassium Cyanide → HCID 58392535, compound

HRID 561546Notes

Reaction equation

CS(O[CH2:6][CH2:7][CH:8]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:9]1[C:17]2[C:12](=[C:13]([CH2:19][S:20][CH3:21])[CH:14]=[C:15]([F:18])[CH:16]=2)[NH:11][CH:10]=1)(=O)=O.[C-:29]#[N:30].[K+]>CN(C=O)C>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH:8]([C:9]2[C:17]3[C:12](=[C:13]([CH2:19][S:20][CH3:21])[CH:14]=[C:15]([F:18])[CH:16]=3)[NH:11][CH:10]=2)[CH2:7][CH2:6][C:29]#[N:30])=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

445 mg (1.01 mmol) of the compound from Example 59A and 131 mg (2.01 mmol) of potassium cyanide were dissolved in 23 ml of DMF and stirred at 80° C. for three days. The mixture was concentrated, and the residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 102 mg (27% of theory) of the title compound. Also obtained were 180 mg (0.47 mmol) of 3-[3-chloro-1-(4-chlorophenyl)propyl]-5-fluoro-7-[(methylsulfanyl)methyl]-1H-indole.

Workup

concentrationThe mixture was concentrated
washwashed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record: ord-8bbdd95085574f1391185350f7a97e2f
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

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