Pyridine → HCID 9821822, compound

HRID 1071863Notes

Reaction equation

HRID 1071863 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[C:9]([CH:10]([C:14]3[CH:19]=[CH:18][C:17]4[O:20][CH2:21][O:22][C:16]=4[CH:15]=3)[C:11]=1[C:12]#[N:13])=[CH:8][CH:7]=[C:6]([N:23]([CH3:25])[CH3:24])[CH:5]=2.N1C=CC=CC=1.[C:32](Cl)(=[O:35])[CH2:33][CH3:34]>ClCCl.CCCCCC.CCOC(C)=O>[C:12]([C:11]1[CH:10]([C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:9]2[C:4](=[CH:5][C:6]([N:23]([CH3:25])[CH3:24])=[CH:7][CH:8]=2)[O:3][C:2]=1[NH:1][C:32](=[O:35])[CH2:33][CH3:34])#[N:13]

Participants

6

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 9923791HCID 9923791, compound

Product 1

HCID 9821822HCID 9821822, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of 2-amino-3-cyano-7-dimethylamino-4-(3,4-methylenedioxyphenyl)-4H-chromene (102 mg, 0.30 mmol) in dichloromethane (5 ml) was added pyridine (0.7 ml) at 0° C., followed by propionyl chloride (0.3 ml). The mixture was then stirred at room temperature for 4 h, diluted with 1:1 hexane/EtOAc (80 ml), washed with water, 2N HCl, water and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (4:1 hexane/EtOAc) to yield the title compound as a yellow solid (16 mg, 14%). 1H NMR (CDCl3): 6.85-6.76 (m, 4H), 6.51-6.48 (m, 1H), 6.31 (m, 1H), 6.00-5.95 (m, 2H), 4.80 (s, 1H), 2.95 (s, 6H), 2.31 (q, J=7.5, 2H), 1.14 (t, J=7.5, 3H).

Workup

  1. washwashed with water, 2N HCl, water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography (4:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-1c3fa5af017348a1b803ea717e1c682e
Source dataset
uspto-grants-2005_06
Patent number
US06906203B1

Reaction notes

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