HCID 22723999, compound → HCID 22724165, compound

HRID 2086880Notes

Reaction equation

HRID 2086880 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([NH:17][C:18]1[CH:19]=[C:20]([N:24]3[C:29](=[O:30])[C:28]([CH2:31][C:32]4[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=4)=[N:27][C:26]4[CH:38]=[CH:39][CH:40]=[N:41][C:25]3=4)[CH:21]=[CH:22][CH:23]=1)=[O:16])[CH:9]=[CH:8]2)(=O)C>Cl>[OH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([NH:17][C:18]1[CH:19]=[C:20]([N:24]3[C:29](=[O:30])[C:28]([CH2:31][C:32]4[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=4)=[N:27][C:26]4[CH:38]=[CH:39][CH:40]=[N:41][C:25]3=4)[CH:21]=[CH:22][CH:23]=1)=[O:16])[CH:9]=[CH:8]2

Participants

3

Reactant 1

HCID 22723999HCID 22723999, compound

Product 1

HCID 22724165HCID 22724165, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4-[3-(6-acetoxy-2-naphthoylamino)phenyl]-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (840 mg) in 3N hydrochloric acid (25 ml) was stirred at room temperature for 2 hours. Then the mixture was concentrated and poured into a mixture of ethyl acetate and aqueous sodium bicarbonate. The organic phase was separated, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was crystallized from ethanol to give 4-[3-(6-hydroxy-2-naphthoylamino)phenyl]-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (127 mg).

Workup

  1. concentrationThen the mixture was concentrated
  2. additionpoured into a mixture of ethyl acetate and aqueous sodium bicarbonate
  3. customThe organic phase was separated
  4. washwashed with aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-0e5f9c21d1b24662a6b1591465b5b750
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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