HCID 54689878, compound → HCID 54689870, compound

HRID 1244165Notes

Reaction equation

HRID 1244165 reaction equation
[OH:1][C:2]1[C:3]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([C:20]#[C:21][CH2:22][CH2:23][CH2:24][OH:25])=[CH:16][CH:15]=3)=[CH:12][S:11][C:4]=2[NH:5][C:6](=[O:10])[C:7]=1[C:8]#[N:9]>C1(C)C=CC=CC=1.CO.[Pd]>[OH:1][C:2]1[C:3]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25])=[CH:16][CH:15]=3)=[CH:12][S:11][C:4]=2[NH:5][C:6](=[O:10])[C:7]=1[C:8]#[N:9]

Participants

5

Reactant 1

HCID 54689878HCID 54689878, compound

Product 1

HCID 54689870HCID 54689870, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a suspension of Pd (BaSO4) (15 mg) in toluene (2 mL) and methanol (1 mL), was added 4-hydroxy-3-[4-(5-hydroxy-pent-1-ynyl)-phenyl]-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (50 mg) in a single portion. The reaction was purged with hydrogen, and stirred under atmosphere hydrogen at rt for 24 h. The mixture was filtered through celite, and rinsed with methanol. The filtrate was concentrated and purified via reverse phase HPLC to afford the titled compound. MS (ESI) m/e 353 (M−H)+; 1H NMR (500 MHz, DMSO-d6): δ 1.31–1.47 (m, 4H), 1.55–1.61 (m, 2H), 1.94 (t, J=7.64 Hz, 2H), 2.58 (t, J=7.64 Hz, 2H), 6.91 (s, 1H), 7.15 (d, J=8.11 Hz, 2H), 7.31 (d, J=8.11 Hz, 2H).

Workup

  1. customThe reaction was purged with hydrogen
  2. filtrationThe mixture was filtered through celite
  3. washrinsed with methanol
  4. concentrationThe filtrate was concentrated
  5. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-a4e9b7ac360b479c979d45be8e5c07c4
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

Loading…