Hydrochloric Acid → HCID 67441245, compound

HRID 1726578Notes

Reaction equation

HRID 1726578 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][S:11]2(=[O:17])=[O:16])[CH:3]=1.[ClH:18]>C(O)C.[Pd]>[ClH:18].[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][S:11]2(=[O:16])=[O:17])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 587773584-Fluoro-2-(1,1-dioxo-1 lambda6-[1,2]thiazinan-2-yl)benzonitrile

Product 1

HCID 67441245HCID 67441245, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Intermediate 75, 4-fluoro-2-(1,1-dioxo-1λ6-[1,2]thiazinan-2-yl)benzonitrile (1.37 g, 5.4 mmol) was dissolved in ethanol (120 mL). To this was added 1N HCl (20 mL) and a catalytic amount of 10% Pd—C. The mixture was shaken under hydrogen at 55 psi for 4 h then filtered through Celite and concentrated to give the title compound as white solid (1.58 g, 100% yield). 1H-NMR (300 MHz, CD3OD) δ ppm: 7.61 (1H, dd, J=8.4, 6.2 Hz), 7.38 (1H, dd, J=9.3, 2.7 Hz), 7.28 (1H, td, J=8.2, 2.7 Hz), 7.26 (2H, dd, J=21.4, 13.7 Hz), 3.93-3.84 (1H, m), 3.50-3.41 (3H, m), 2.40-2.31 (2H, m), 2.04-1.96 (2H, m). LCMS [M+H]+ calcd for C11H16N2O6FS: 259.087; found: 259.24.

Workup

  1. filtrationthen filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-96b058dfca034c8e82fcebd30517103e
Source dataset
uspto-grants-2009_02
Patent number
US07491819B1

Reaction notes

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