HCID 10910039, compound → HCID 57413701, compound

HRID 333923Notes

Reaction equation

HRID 333923 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH3:16])[C:12]([NH2:15])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.[CH3:18][C:19]1[O:23][C:22]([CH2:24][CH2:25][C:26](Cl)=[O:27])=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH3:1][N:2]([CH3:17])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]([CH3:16])[C:12]([NH:15][C:26](=[O:27])[CH2:25][CH2:24][C:22]3[O:23][C:19]([CH3:18])=[CH:20][CH:21]=3)=[N:13][CH:14]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 10910039HCID 10910039, compoundHCID 68008562HCID 68008562, compound

Product 1

HCID 57413701HCID 57413701, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 5-(4-(dimethylamino)phenyl)-3-methylpyridin-2-amine (120b, 2.27 g, 10.0 mmol) in pyridine (30 ml) was added with 3-(5-methylfuran-2-yl)propanoyl chloride (1.90 g, 11.0 mmol) and then stirred at room temperature for further 16 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give N-(5-(4-(Dimethylamino)phenyl)-3-methylpyridin-2-yl)-3-(5-methylfuran-2-yl) propanamide (120): 1H NMR (500 MHz, DMSO-d6):δ: 9.99 (s, 1H), 8.46 (s, 1H), 7.84 (s, 1H), 7.55 (m, 2H), 6.81 (m, 2H), 5.98 (s, 1H), 5.94 (s, 1H), 2.94 (s, 6H), 2.87 (t, 2H), 2.65 (t, 2H), 2.21 (s, 3H), 2.16 (s, 3H).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4(s)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d9e3e06a13b840c6bcb9ed4cb0183c60
Source dataset
uspto-grants-2014_11
Patent number
US08883793B2

Reaction notes

Loading…