Hydrochloric Acid → HCID 66727494, compound

HRID 1361265Notes

Reaction equation

HRID 1361265 reaction equation
[CH3:1][N:2]([CH3:15])[S:3]([NH:6][C:7]1[N:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)(=[O:5])=[O:4].C(OCC)(=O)C.[ClH:22]>CO.O1CCOCC1.[Pd]>[ClH:22].[ClH:22].[CH3:1][N:2]([CH3:15])[S:3]([NH:6][C:7]1[N:12]=[CH:11][C:10]([CH2:13][NH2:14])=[CH:9][CH:8]=1)(=[O:4])=[O:5]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 55211232HCID 55211232, compound

Product 1

HCID 66727494HCID 66727494, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-(dimethylaminosulfonylamino)-3-cyanopyridine (250 mg, 1.1 mmol) in a mixture of MeOH (25 mL) and 4 N HCl in dioxane (1 mL) was hydrogenated over 10% Pd/C catalyst using a continuous flow hydrogenation apparatus (conditions: flow rate 1.0 mL/minute, 25° C., 1 atmosphere). The reaction was monitored by TLC (ethyl acetate). The methanol was concentrated in vacuo to afford the title compound.

Workup

  1. customa continuous flow hydrogenation apparatus (conditions: flow rate 1.0 mL/minute, 25° C., 1 atmosphere)
  2. concentrationThe methanol was concentrated in vacuo

Sources & evidence

ORD record
ord-6df055f770d345fca58f50f6da2fb628
Source dataset
uspto-grants-2011_02
Patent number
US07879873B2

Reaction notes

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