Isopropanol → HCID 21912921, compound

HRID 1352639Notes

Reaction equation

HRID 1352639 reaction equation
C(O)(C)C.[NH2:5][C:6]1[C:11]2[N:12]=[C:13]([CH2:25][CH2:26][CH3:27])[N:14]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[C:10]=2[C:9]([C:28]#[C:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:8][N:7]=1>[Pd].CO>[NH2:5][C:6]1[C:11]2[N:12]=[C:13]([CH2:25][CH2:26][CH3:27])[N:14]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[C:10]=2[C:9]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:8][N:7]=1

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 21913624HCID 21913624, compound

Product 1

HCID 21912921HCID 21912921, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Solid palladium on carbon (0.5 g of 10%) was added to a Parr vessel and then wetted with isopropanol (1 mL). N-{2-[2-(4-Amino-7-hex-1-ynyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)ethoxy]ethyl}methanesulfonamide (˜0.5 g) was added to the vessel followed by the addition of methanol (˜10 mL). The vessel was placed on a shaker and placed under hydrogen pressure (50 psi, 3.4×105 Pa). After 20 hours the reaction mixture was filtered through a layer of CELITE filter agent to remove the catalyst and the filter cake was washed with methanol (˜100 mL). The filtrate was concentrated under reduced pressure. The residue was purified by chromatography (silica gel eluting with 95:5 dichloromethane:methanol) to provide N-{2-[2-(4-amino-7-hexyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)ethoxy]ethyl}methanesulfonamide as a clear oil.

Workup

  1. filtrationAfter 20 hours the reaction mixture was filtered through a layer of CELITE filter agent
  2. customto remove the catalyst
  3. washthe filter cake was washed with methanol (˜100 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by chromatography (silica gel eluting with 95:5 dichloromethane:methanol)

Sources & evidence

ORD record
ord-d8fbb83b0c1d4aaba2d667a66ff4933b
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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