Hydrochloric Acid → HCID 53824544, compound

HRID 2416725Notes

Reaction equation

HRID 2416725 reaction equation
N[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:28]=[CH:27][C:16]3[CH2:17][CH:18]([CH2:23][C:24]([OH:26])=[O:25])[C:19](=[O:22])[NH:20][CH2:21][C:15]=3[CH:14]=2)[CH:3]=1.Cl.O1CCO[CH2:32][CH2:31]1.[CH2:36](N(CC)CC)C>C(O)C>[N:5]1[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:28]=[CH:27][C:16]2[CH2:17][CH:18]([CH2:23][C:24]([O:26][CH2:31][CH3:32])=[O:25])[C:19](=[O:22])[N:20]([CH3:36])[CH2:21][C:15]=2[CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 22632125HCID 22632125, compound

Product 1

HCID 53824544HCID 53824544, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (±)-8-[3-[(4-amino-2-pyridyl)amino]-1-propyloxy]-3-oxo-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetic acid (0.27 g, 0.7 mmol) and 4 M HCl in dioxane (0.2 mL, 0.8 mmol) in ethanol (10 mL) was heated to reflux. After 72 hr, the reaction was concentrated and the residue was partitioned between EtOAc and aqueous K2CO3. The organic phase was washed with brine, dried (MgSO4), and concentrated. The residue was dissolved in toluene (5 mL) and triethylamine (0.35 mL, 2.5 mmol). and the resulting solution was heated to reflux. After 18 hr, the reaction was concentrated under vacuum to give the title compound (0.20 g, 69%) as a tan foam: MS (ES) m/e 413.4 (M+H)+. Anal. Calcd for C22H28N4O4.0.25 H2O: C, 63.37; H, 6.89; N,13.44. Found: C, 63.32; H, 7.17; N, 13.05.

Workup

  1. concentrationthe reaction was concentrated
  2. customthe residue was partitioned between EtOAc and aqueous K2CO3
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in toluene (5 mL)
  7. temperatureand the resulting solution was heated to reflux
  8. waitAfter 18 hr
  9. concentrationthe reaction was concentrated under vacuum

Sources & evidence

ORD record
ord-32b92acacf0c49fdbd584a2b87cabc27
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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