Hydrochloric Acid → HCID 71241085, compound

HRID 1753771Notes

Reaction equation

HRID 1753771 reaction equation
Cl[C:2]1[O:3][C:4]([C:7]2[CH:8]=[C:9]([C:13]3[C:14]([O:19]C)=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:10]=[CH:11][CH:12]=2)=[CH:5][N:6]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1)[NH2:26].Cl>CC(O)C>[CH3:31][O:30][C:28]1[CH:27]=[C:25]([NH:26][C:2]2[O:3][C:4]([C:7]3[CH:8]=[C:9]([C:13]4[C:14](=[O:19])[NH:15][CH:16]=[CH:17][CH:18]=4)[CH:10]=[CH:11][CH:12]=3)=[CH:5][N:6]=2)[CH:24]=[C:23]([O:22][CH3:21])[CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 663013,5-DimethoxyanilineHCID 71239758HCID 71239758, compound

Product 1

HCID 71241085HCID 71241085, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3-{3-[2-(3,5-Dimethoxy-phenylamino)-oxazol-5-yl]-phenyl}-1H-pyridin-2-one 219 was prepared as for intermediate I-f above from 3-[3-(2-chloro-oxazol-5-yl)-phenyl]-2-methoxy-pyridine VI-c (40 mg, 0.150 mmol) with 3,5-dimethoxyaniline (29 mg, 0.190 mmol) and HCl (2M in ether, 120 μL, 0.23 mmol) in iPrOH (4 mL). The crude reaction mixture was evaporated under reduced pressure and the residue treated with a saturated solution of NaHCO3 and EtOAc. A precipitate formed from the biphasic mixture and was filtered off and dried to give the compound 219 product as a beige solid (19 mg, 33%). 1H NMR (300 MHz, DMSO-d6) δ 11.86 (s, 1H), 10.35 (s, 1H), 7.96 (s, 1H), 7.70 (dd, J=2.0, 6.9 Hz, 1H), 7.60-7.41 (m, 5H), 6.89 (d, J=2.0 Hz, 2H), 6.32 (t, J=6.7 Hz, 1H), 6.13 (s, 1H), 3.73 (s, 6H). ESI+ MS m/z 390 (M+H)+. Retention time=3.45 min (method 1).

Workup

  1. customThe crude reaction mixture
  2. customwas evaporated under reduced pressure
  3. additionthe residue treated with a saturated solution of NaHCO3 and EtOAc
  4. customA precipitate formed from the biphasic mixture
  5. filtrationwas filtered off
  6. customdried

Sources & evidence

ORD record
ord-f2009c0eb75a498cbd5ff87c18a671df
Source dataset
uspto-grants-2015_10
Patent number
US09168245B2

Reaction notes

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