3-Aminopyridine → HCID 44600698, compound

HRID 1962399Notes

Reaction equation

HRID 1962399 reaction equation
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[O:6][C:5]=1[NH:15][C@H:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:17][CH3:18])(=O)[CH3:2].[NH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1>C(#N)C>[C:19]1([C@@H:16]([NH:15][C:5]([C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:14])[N:25]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[C:1]=2[CH3:2])=[O:6])[CH2:17][CH3:18])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 57733336HCID 57733336, compound

Product 1

HCID 44600698HCID 44600698, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 4-acetyl-3-((S)-1-phenyl-propylamino)-isochromen-1-one (100 mg) and 3-aminopyridine (400 mg, excess) in acetonitrile (0.2 mL) was heated under microwave irradiation at 170° C. for 15 min. The reaction mixture was partitioned between water (20 ml) and ethyl acetate (20 ml), and the organic phase was washed with water (3×10 ml). The product was extracted into aqueous phase with aq. 2M HCl (10 ml), the aqueous solution was neutralised with aq. 10% Na2CO3 and extracted again with ethyl acetate and evaporated. The obtained residue was purified by flash chromatography on SiO2 (5 g, gradient heptane-ethyl acetate, the product came out with 100% ethyl acetate) to give 37 mg of oil, which was precipitated from methanol (0.1 mL) and water (10 mL) with sonication for 10 min. The title compound was separated by filtration to give 10 mg of brown solid. LC-MS (m/z) 398.1 (MH+); tR=1.06. 1H NMR (250 MHz, 70° C., DMSO-d6): 0.93 (t, J=7.4 Hz, 3H, Me of Et), 1.72-1.88 (overlapping m, CH2 of Et), 1.85 (overlapping s, 3H, Me), 4.97 (q (dt), J=8 Hz, J=6.9 Hz, 1H, CHNH), 7.23 (m, 1H), 7.28-7.42 (m, 5H), 7.49 (t, J=7.6 Hz, 1H), 7.59 (dd, J=4.8 Hz, J=8.1 Hz, 1H), 7.69 (t, J=7.7 Hz, 1H), 7.76 (d of dd, J=8.1 Hz, J=2.4 Hz, J=1.4 Hz, 1H), 8.21 (dd, J=8 Hz, J=0.8 Hz, 1H), 8.49 (d, J=2.4 Hz), 8.67 (dd, J=4.7 Hz, J=2.4 Hz, 1H), 8.72 (br d, J=8.2 Hz, NHCO).

Workup

  1. customThe reaction mixture was partitioned between water (20 ml) and ethyl acetate (20 ml)
  2. washthe organic phase was washed with water (3×10 ml)
  3. extractionThe product was extracted into aqueous phase with aq. 2M HCl (10 ml)
  4. extractionextracted again with ethyl acetate
  5. customevaporated
  6. customThe obtained residue was purified by flash chromatography on SiO2 (5 g, gradient heptane-ethyl acetate

Sources & evidence

ORD record
ord-f257607fdf7341578c6a8baf57e0be38
Source dataset
uspto-grants-2013_04
Patent number
US08415356B2

Reaction notes

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