Sodium Cyanide → HCID 71504394, compound

HRID 929362Notes

Reaction equation

HRID 929362 reaction equation
Cl[C:2]1[CH:3]=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([C:14]1[C:15]([F:35])=[C:16]([N:22](S(CCC)(=O)=O)[S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])[CH:17]=[C:18]([F:21])[C:19]=1[F:20])=[O:13])=[CH:7][CH:6]=2.[C-:36]#[N:37].[Na+]>CN(C=O)C.O>[C:36]([C:2]1[CH:3]=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([C:14]1[C:15]([F:35])=[C:16]([NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:24])=[O:25])[CH:17]=[C:18]([F:21])[C:19]=1[F:20])=[O:13])=[CH:7][CH:6]=2)#[N:37]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 86677184HCID 86677184, compound

Product 1

HCID 71504394HCID 71504394, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-(3-(3-chloroquinoxaline-6-carbonyl)-2,4,5-trifluorophenyl)-N-(propylsulfonyl)propane-1-sulfonamide (50 mg, 0.1 mmol, 1.0 eq.) and NaCN (9.8 mg, 0.002 mol, 2.0 eq.) in DMF (10 mL) was heated at 100° C. for 10 h under N2 protection. The mixture was cooled, diluted with water and extracted with EA (20 mL×3). The combined organic layers were washed with water, saline and dried over Na2SO4, filtered, and concentrated. The resulting residue was purified by flash column chromatography (PE/EA=4/1, v/v) to afford N-(3-(3-cyanoquinoxaline-6-carbonyl)-2,4,5-trifluorophenyl)propane-1-sulfonamide. LRMS (MAT) m/z calculated 435.1, found 435.0. 1H NMR (DMSO-d6, 400 MHz) δ 10.11 (brs, 1 H), 9.52 (s, 1 H), 8.75 (s, 1 H), 8.52 (d, 1 H), 8.41 (d, 1 H), 7.79 (m, 1 H), 3.22 (t, 2 H), 1.72 (m, 2 H), 0.95 (t, 3 H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with EA (20 mL×3)
  3. washThe combined organic layers were washed with water, saline
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash column chromatography (PE/EA=4/1

Sources & evidence

ORD record
ord-a5a7f1d2b7094d018a005770bd13c3df
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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