2-Aminopyridine → HCID 44234336, compound

HRID 391271Notes

Reaction equation

HRID 391271 reaction equation
CO[C:3]([CH:5]1[CH2:11][CH2:10][O:9][C:8]2[CH:12]=[C:13]([Cl:17])[C:14]([Cl:16])=[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]([Cl:17])[C:14]([Cl:16])=[CH:15][C:7]=2[C:6]1=[O:18])=[O:4]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 58775910HCID 58775910, compound

Product 1

HCID 44234336HCID 44234336, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

7,8-Dichloro-5-oxo-2,3,4,5-tetrahydro-benzo[b]oxepine-4-carboxylic acid methyl ester (0.2 mmol) and 2-aminopyridin (0.2 mmol) were dissolved in 1 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. The remaining residue was purified via HPLC (Chromolith prep. RP18, Solvent A water:acetonitrile 90:10+0.1% formic acid, solvent B: water:acetonitrile 10:90+0.1% formic acid, flow: t=0 min 25 ml/min, t=1 min 50 ml/min, gradient: t=0 min 10% B, t=1 min 10% B, t=2 min 10% B, t=2.2 min 20% B, t=7.5 min 50% B, t=7.6 min 100% B, t=8.5 min 100% B). After evaporation of the solvent in vacuo 7,8-Dichloro-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 14%. LC-MS: 1.9 min, 351.0 (MH+), 1H-NMR: (DMSO-d6, 500 MHz): □ [ppm]: 10.543 (s, 1H), 8.304 (s, 1H), 8.135 (d, 1H, J=8.1 Hz), 7.809 (t, 1H, J=7.6 Hz), 7.758 (s, 1H), 7.524 (s, 1H), 7.114 (s, 1H), 4.652 (m, 1H, J=2.8 Hz), 4.360 (t, 1H, J=8.9 Hz), 4.042 (m, 1H, J=4.9 Hz), 2.512 (m, 2H, J=1.8 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. customThe remaining residue was purified via HPLC (Chromolith prep. RP18, Solvent A water:acetonitrile 90:10+0.1% formic acid, solvent B: water:acetonitrile 10:90+0.1% formic acid, flow: t=0 min 25 ml/min, t=1 min 50 ml/min, gradient: t=0 min 10% B, t=1 min 10% B, t=2 min 10% B, t=2.2 min 20% B, t=7.5 min 50% B, t=7.6 min 100% B, t=8.5 min 100% B)
  9. customAfter evaporation of the solvent in vacuo 7,8-Dichloro-5-oxo-2,3,4,5-tetrahydro-benzo[b]oxepine-4-carboxylic acid pyridine-2-ylamide
  10. customwas obtained as a white powder in a yield of 14%
  11. custom1.9 min, 351.0 (MH+)

Sources & evidence

ORD record
ord-fca62ad5815349bdb57a8f6cf2221eb7
Source dataset
uspto-grants-2013_02
Patent number
US08383838B2

Reaction notes

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