Quinoline → HCID 58387874, compound

HRID 2080234Notes

Reaction equation

HRID 2080234 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]2[CH:28]=[CH:27][C:12]([CH2:13][NH:14][C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[N:23]=[CH:22][CH:21]=[CH:20]4)=[O:16])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C2C(=CC=CC=2)C=CC=1>O1CCCC1>[CH:8](/[C:9]1[CH:28]=[CH:27][C:12]([CH2:13][NH:14][C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[CH:20]3)=[O:16])=[CH:11][CH:10]=1)=[CH:7]/[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7047QuinolineHCID 67119620HCID 67119620, compound

Product 1

HCID 58387874HCID 58387874, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of quinoline-6-carboxylic acid 4-phenylethenyl-benzylamide described in Preparation Example E+-5 (48 mg, 0.13 mmol), quinoline (26 mg, 0.20 mmol) and tetrahydrofuran (2 mL) was added Linear catalyst (5.0 mg), and the solution was stirred under hydrogen atmosphere at room temperature for 1 hour. The interior of the reaction system was changed to nitrogen atmosphere, then, filtration was carried out through Celite pad. The filtrate was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4), and the title compound (45 mg, 0.12 mmol, 92%) was obtained as a colorless oil.

Workup

  1. filtrationfiltration
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-93ac92695b624efeb73bd9e589f9ca52
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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