HCID 72194554, compound → HCID 72194553, compound

HRID 594159Notes

Reaction equation

HRID 594159 reaction equation
[CH2:1]([N:5]([C:23]1[C:28]([CH3:29])=[CH:27][C:26]([C:30]([CH3:32])=[CH2:31])=[CH:25][N:24]=1)[S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH:2]([CH3:4])[CH3:3]>C(OCC)(=O)C.CO.[Pd]>[CH2:1]([N:5]([C:23]1[C:28]([CH3:29])=[CH:27][C:26]([CH:30]([CH3:32])[CH3:31])=[CH:25][N:24]=1)[S:6]([C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)=[CH:13][CH:14]=1)(=[O:7])=[O:8])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 1

HCID 72194554HCID 72194554, compound

Product 1

HCID 72194553HCID 72194553, compoundYield 73.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-isobutyl-N-(3-methyl-5-(prop-1-en-2-yl)pyridin-2-yl)-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide (83 mg, 0.18 mmol) was dissolved in ethyl acetate (3 mL) and methanol (3 mL). The reaction was hydrogenated using an H-cube flow hydrogenator (settings: room temperature, 1 bar, 1 mL/min flow rate) and a 10% Pd/C CatCart as the catalyst. Two clean fractions of product were collected along with a third impure fraction, the impure fraction was then purified by mass directed autoprep (formic acid modifier). The two clean product fractions and purified third fraction were then combined and evaporated to give the title compound (61 mg). LCMS (2 min, formic) Rt 1.45 min, m/z (ES+) 461 (M+H).

Workup

  1. customan H-cube flow hydrogenator (settings: room temperature, 1 bar, 1 mL/min flow rate)
  2. customTwo clean fractions of product were collected along with a third impure fraction
  3. customthe impure fraction was then purified by mass
  4. customThe two clean product fractions and purified third fraction
  5. customevaporated

Sources & evidence

ORD record
ord-3fd71b69399b45b5910a349562488e63
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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