Potassium Cyanide → HCID 67434460, compound

HRID 245577Notes

Reaction equation

[F:1][C:2]1[C:3]2[O:28][N:27]=[C:26](S(C)(=O)=O)[C:4]=2[CH:5]=[C:6]2[C:19]=1[N:18]1[CH2:20][C@@H:21]([CH3:25])[O:22][C@@H:23]([CH3:24])[C@@H:17]1[C:8]1([C:13](=[O:14])[NH:12][C:11](=[O:15])[NH:10][C:9]1=[O:16])[CH2:7]2.[C-:33]#[N:34].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C>[F:1][C:2]1[C:3]2[O:28][N:27]=[C:26]([C:33]#[N:34])[C:4]=2[CH:5]=[C:6]2[C:19]=1[N:18]1[CH2:20][C@@H:21]([CH3:25])[O:22][C@@H:23]([CH3:24])[C@@H:17]1[C:8]1([C:13](=[O:14])[NH:12][C:11](=[O:15])[NH:10][C:9]1=[O:16])[CH2:7]2

Participants

Conditions

Temperature: 85 °C

Procedure

To a stirred solution of (2R,4S,4aS)-rel-11-fluoro-2,4-dimethyl-8-(methylsulfonyl)-1,2,4,4a-tetrahydro-2′H,6H-spiro[1,4-oxazino[4,3-a][1,2]oxazolo[4,5-g]quinoline-5,5′-pyrimidine]-2′,4′,6′(1′H,3′H)-trione (Example 182, 1.0 g, 2.15 mmol) in DMF was added KCN (700 mg, 10.75 mmol) followed by 18-crown-6 (catalytic) and the mixture was heated at 85° C. for 12 hours. The reaction mixture was cooled to room temperature and precipitated with diethyl ether (repeated twice to remove complete DMF). The precipitate was dissolved in EtOAc (50 mL) and washed with water (2×10 mL), dried over anhydrous sodium sulfate and, filtered, concentrated. The residue was purified by ‘combiflash instrument’ to give product as a pale yellow solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
customprecipitated with diethyl ether (
customto remove complete DMF)
dissolutionThe precipitate was dissolved in EtOAc (50 mL)
washwashed with water (2×10 mL)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by ‘combiflash instrument’
customto give product as a pale yellow solid

Sources & evidence

ORD record: ord-ef71a7a0d4174fed8fd434c33e1a6a71
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658641B2

Reaction notes

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