2-Aminopyridine → HCID 44234338, compound

HRID 391275Notes

Reaction equation

HRID 391275 reaction equation
CO[C:3]([CH:5]1[CH2:11][CH2:10][O:9][C:8]2[CH:12]=[C:13]([CH2:16][CH3:17])[CH:14]=[CH:15][C:7]=2[C:6]1=[O:18])=[O:4].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1>C1(C)C(C)=CC=CC=1>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[NH:19][C:3]([CH:5]1[CH2:11][CH2:10][O:9][C:8]2[CH:12]=[C:13]([CH2:16][CH3:17])[CH:14]=[CH:15][C:7]=2[C:6]1=[O:18])=[O:4]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 66840950HCID 66840950, compound

Product 1

HCID 44234338HCID 44234338, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

8-Ethyl-5-oxo-2,3,4,5-tetrahydro-benzo[b]oxepine-4-carboxylic acid methyl ester (0.6 mmol) and 2-aminopyridin (0.6 mmol) were dissolved in 2.5 ml xylene. Reaction was performed by microwave irradiation for one hour at 150° C. The solution obtained from this reaction was cooled to room temperature and extracted by 2 mol/l hydrochloric acid and ethyl acetate. The ethyl acetate extract was dried over sodiumsulfate and the solvent removed in vacuo. After evaporation of the solvent in vacuo 8-Ethyl-5-oxo-2,3,4,5-tetrahydro-benzo[b]oxepine-4-carboxylic acid pyridine-2-ylamide was obtained as a white powder in a yield of 5%. LC-MS: 1.8 min, 311.2 (MH+), 1H-NMR: (DMSO-d6, 500 MHz): □ [ppm]: 10.543 (s, 1H), 8.296 (s, 1H), 8.152 (d, 1H, J=8.1 Hz), 7.798 (t, 1H, J=7.2 Hz), 7.605 (m, 1H, J=8.1 Hz), 7.102 (t, 1H, J=6.3 Hz), 7.032 (m, 1H, J=8.1 Hz), 6.983 (s, 1H), 4.594 (m, 1H, J=3.0 Hz), 4.364 (t, 1H, J=4.8 Hz), 3.942 (m, 1H, J=5.2 Hz), 2.640 (q, 2H, J=7.7 Hz), 2.512 (t, 2H, J=1.7 Hz), 1.193 (t, 3H, J=7.5 Hz)

Workup

  1. customReaction
  2. customwas performed by microwave irradiation for one hour at 150° C
  3. customThe solution obtained from this reaction
  4. extractionextracted by 2 mol/l hydrochloric acid and ethyl acetate
  5. extractionThe ethyl acetate extract
  6. dry with materialwas dried over sodiumsulfate
  7. customthe solvent removed in vacuo
  8. customAfter evaporation of the solvent in vacuo 8-Ethyl-5-oxo-2,3,4,5-tetrahydro-benzo[b]oxepine-4-carboxylic acid pyridine-2-ylamide
  9. customwas obtained as a white powder in a yield of 5%
  10. custom1.8 min, 311.2 (MH+)

Sources & evidence

ORD record
ord-e9c307d8ced64648bc37b51c8508d214
Source dataset
uspto-grants-2013_02
Patent number
US08383838B2

Reaction notes

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