Pyridine → HCID 69001486, compound

HRID 1071865Notes

Reaction equation

HRID 1071865 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]2[O:10][CH2:11][O:12][C:5]2=[CH:4][C:3]=1[C:13]1[O:14][C:15]2[C:20]([CH2:21][CH:22]=1)=[CH:19][CH:18]=[C:17]([N:23]([CH3:25])[CH3:24])[CH:16]=2.N1C=CC=CC=1.[CH2:32]([O:34][C:35](Cl)=[O:36])[CH3:33].CCCCCC.[CH3:44][CH2:45][O:46][C:47](C)=[O:48]>C(Cl)Cl>[C:8]([C:7]1[C:2]([N:1]([C:47]([O:46][CH2:45][CH3:44])=[O:48])[C:35]([O:34][CH2:32][CH3:33])=[O:36])=[C:3]([C:13]2[O:14][C:15]3[C:20]([CH2:21][CH:22]=2)=[CH:19][CH:18]=[C:17]([N:23]([CH3:25])[CH3:24])[CH:16]=3)[CH:4]=[C:5]2[O:12][CH2:11][O:10][C:6]=12)#[N:9]

Participants

6

Reactant 4

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 21226206Ethyl acetate hexaneHCID 69004803HCID 69004803, compound

Product 1

HCID 69001486HCID 69001486, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-3-cyano-7-dimethylamino-4-(methylenedioxy)phenyl-4H-chromene (53 mg, 0.16 mmol) in methylenechloride (3 ml) was added pyridine (0.06 ml, 0.74 mmol), followed by ethylchloroformate (0.045 ml, 0.47 mmol). The mixture was stirred at room temperature overnight, then diluted with 1:1 hexane/EtOAc (45 ml), washed with water, 2N HCl, water and brine. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (3:1 hexane/EtOAc) to yield the title compound as a yellow solid (5 mg, 7%). 1H NMR (CDCl3): 6.84-6.61 (m, 4H), 6.49-6.42 (m, 1H), 6.30 (m, 1H), 5.93,5.92 (2s, 2H), 4.74 (s, 1H), 4.36 (m, 4H), 2.93 (s, 6H), 1.31 (t, J=7.2, 6H).

Workup

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

Sources & evidence

ORD record
ord-737fa9c48b3c4e83a7c402910675037f
Source dataset
uspto-grants-2005_06
Patent number
US06906203B1

Reaction notes

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