Hydrochloric Acid → 1-(4-Fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)phenyl)methanamine

HRID 1093040Notes

Reaction equation

HRID 1093040 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N:10]2[CH2:14][C:13]([CH3:16])([CH3:15])[N:12]([CH3:17])[S:11]2(=[O:19])=[O:18])[CH:3]=1.Cl>C(Cl)Cl.C(OCC)(=O)C.C(O)C.[Pd]>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([N:10]2[CH2:14][C:13]([CH3:16])([CH3:15])[N:12]([CH3:17])[S:11]2(=[O:19])=[O:18])[CH:3]=1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 579049514-Fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)benzonitrile

Product 1

HCID 579048021-(4-Fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)phenyl)methanamine

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)benzonitrile (3.34 g, 11.8 mmol) in CH2Cl2 (30 mL), ethyl acetate (30.0 mL) and ethanol (30.0 mL) was added 1N HCl (12 mL) followed by 10% palladium on carbon (0.377 g, 3.54 mmol). The mixture was shaken under H2 at 50 psi for 22 h then filtered over CELITE® and concentrated. The solids were triturated with H2O and removed by filtration. The aqueous solution was washed with ethyl acetate and lyophilized to give the title compound, as the HCl salt, as a white powder (3.44 g, 90% yield). LCMS (M+H) calcd for C12H19FN3O2S: 288.11; found: 288.19. 1H NMR (300 MHz, DMSO) δ: 8.35 (2H, brs), 7.71 (1H, dd, J=8.6, 6.4 Hz), 7.54 (1H, dd, J=9.9, 2.6 Hz), 7.43 (1H, td, J=8.4, 2.6 Hz), 4.19 (2H, s), 3.75 (2H, s), 2.63 (3H, s), 1.35 (6H, s).

Workup

  1. filtrationthen filtered over CELITE®
  2. concentrationconcentrated
  3. customThe solids were triturated with H2O
  4. customremoved by filtration
  5. washThe aqueous solution was washed with ethyl acetate

Sources & evidence

ORD record
ord-572e25877f854ff59027479df912b328
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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