HCID 23505276, compound → HCID 67172591, compound

HRID 551114Notes

Reaction equation

HRID 551114 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([CH:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]([OH:30])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.CO[CH:33]1[CH2:37][CH:36]=[C:35](OC)O1>C(O)(=O)C>[OH:30][C:9]1[C:10]([CH:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:2]([N:1]2[CH:33]=[CH:37][CH:36]=[CH:35]2)=[C:3]2[C:8]=1[N:7]=[CH:6][CH:5]=[CH:4]2

Participants

4

Reactant 2

HCID 23505276HCID 23505276, compoundHCID 67171864N-[(5-amino-8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide

Product 1

HCID 67172591HCID 67172591, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-[(5-amino-8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide (150 mg, 0.37 mmol), 2,5-dimethoxydihydrofuran (50 mg, 0.37 mmol) in acetic acid (1 ml) were heated at 65 C for 40 min. The reaction mixture was concentrated, dissolved in ethylacetate, washed with aq. Sodium bicarbonate and dried over sodium sulfate. The solvent was removed in vacuo to afford N-[[8-hydroxy-5-(1H-pyrrol-1-yl)quinolin-7-yl](phenyl)methyl]-2-phenoxyacetamide as a tan solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in ethylacetate
  3. washwashed with aq. Sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3abfd285430941ea87d582edb3cbf465
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

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