Hydrochloric Acid → 4-[(S)-2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridine-3-carbaldehyde

HRID 929143Notes

Reaction equation

HRID 929143 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:24])[CH2:9][NH:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([O:17]C)[C:12]=2[CH:19]2OCC[O:20]2)[CH:5]=[CH:6][CH:7]=1.O.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:24])[CH2:9][NH:10][C:11]2[CH:16]=[CH:15][NH:14][C:13](=[O:17])[C:12]=2[CH:19]=[O:20])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 59762183(S)-1-(3-Chloro-phenyl)-2-(3-[1,3]dioxolan-2-yl-2-methoxy-pyridin-4-ylamino)-ethanol

Product 1

HCID 597621124-[(S)-2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridine-3-carbaldehydeYield 11%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of (S)-1-(3-chloro-phenyl)-2-(3-[1,3]dioxolan-2-yl-2-methoxy-pyridin-4-ylamino)-ethanol (223 mg, 0.64 mmol) and H2O (0.75 mL) was added HCl solution in dioxane (4 M, 10 mL). After it was heated at 70° C. for 4 h, the reaction mixture was evaporated to dryness. HPLC purification of the residue afforded the title compound (20.1 mg, 11%). 1H NMR (DMSO-d6) δ 3.37 (m, 1H) 3.58 (m, 1H), 4.58 (m, 1H), 5.95 (d, J=6 Hz, 1H), 7.30-7.40 (3H), 7.49 (s, 1H), 9.94 (s, 1H, CHO), 10.30 (m, 1H, NH), 10.95 (m, 1H, 1H). ESI-MS m/z 293.3 (MH+).

Workup

  1. customthe reaction mixture was evaporated to dryness
  2. customHPLC purification of the residue

Sources & evidence

ORD record
ord-32b38f9a503b4c5eba6e38d35dafcb74
Source dataset
uspto-grants-2016_03
Patent number
US09290503B2

Reaction notes

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