Pyridine → HCID 131726425, compound

HRID 1785866Notes

Reaction equation

HRID 1785866 reaction equation
[CH3:1][C@H:2]1[CH2:11][C@@H:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:19](=[O:21])[CH3:20].[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27](Cl)=[O:28].N1C=CC=CC=1>C1(C)C=CC=CC=1>[C:19]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C@H:10]([N:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:27]([C:23]2[O:22][CH:26]=[CH:25][CH:24]=2)=[O:28])[CH2:11][C@@H:2]1[CH3:1])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 682422-Furancarbonyl chlorideHCID 667862HCID 667862, compound

Product 1

HCID 131726425HCID 131726425, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A round bottom flask under nitrogen atmosphere was charged with cis-(2-methyl-4-phenylamino-3,4-dihydro-2H-quinolin-1-yl)-ethanone (0.163 g, 0.58 mmol, 1.0 equiv) and 2-furoyl chloride (0.285 mL, 2.9 mmol, 5.0 equ), pyridine (1.0 equiv.) and dry toluene (3 mL). The solution was heated to 90° C. for 15 h. The reaction mixture was evaporated in vacuo. The residue was purified by Biotage flash system (50% hexane/50% ethyl acetate) to yield the cis isomer 40% yield.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customThe residue was purified by Biotage flash system (50% hexane/50% ethyl acetate)
  3. customto yield the cis

Sources & evidence

ORD record
ord-a3fb00f4f2f34bf4924744098467e41c
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

Loading…