HCID 69693723, compound → HCID 10230591, compound

HRID 896694Notes

Reaction equation

HRID 896694 reaction equation
[C:1]([C:3]([CH3:39])([CH3:38])[C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]3[CH:15]=[C:16]([CH:20]=[C:21]([C:28]4[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][CH:29]=4)[C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH:17]=[CH:18][CH:19]=3)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)#[N:2]>C1COCC1.[Pd]>[C:1]([C:3]([CH3:39])([CH3:38])[C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]3[CH:15]=[C:16]([CH2:20][CH:21]([C:28]4[CH:29]=[CH:30][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:32][CH:33]=4)[C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH:17]=[CH:18][CH:19]=3)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)#[N:2]

Participants

4

Reactant 1

HCID 69693723HCID 69693723, compound

Product 1

HCID 10230591HCID 10230591, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-{3-[6-(cyano-dimethyl-methyl)-quinolin-8-yl]-phenyl}-N-isopropyl-2-(4-methanesulfonyl-phenyl)-acrylamide from Step 3 (20 mg, 0.038 mmol) in THF (1 mL) containing Pd/C (10%, 9 mg) was stirred under H2 (50 psi) for 18 h. Filtration on celite, evaporation, and purification on HPLC (u-porasil ethyl acetate/hexane, 70:30 to 100:0, over 30 min.) afforded the 3-{3-[6-(cyano-dimethyl-methyl)-quinolin-8-yl]-phenyl}-N-isopropyl-2-(4-methanesulfonyl-phenyl)-propionamide compound as a foam.

Workup

  1. filtrationFiltration
  2. customon celite, evaporation, and purification on HPLC (u-porasil ethyl acetate/hexane, 70:30 to 100:0, over 30 min.)

Sources & evidence

ORD record
ord-0d483cd997be40b9b568e443a2df6fd7
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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