Phenol → HCID 135407194, compound

HRID 324270Notes

Reaction equation

HRID 324270 reaction equation
[OH:1][C:2]1[CH2:10][CH2:9][N:8]2[C:4](=[N:5][C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=32)[C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[C:20]1(O)[CH:25]=CC=[CH:22][CH:21]=1>>[C:18]1([O:17][C:15]([C:3]2[C:4]3=[N:5][C:6]4[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=4[N:8]3[CH2:9][CH2:10][C:2]=2[OH:1])=[O:16])[CH:22]=[CH:21][CH:20]=[CH:25][CH:19]=1

Participants

3

Reactant 2

HCID 996PhenolHCID 135452099HCID 135452099, compound

Product 1

HCID 135407194HCID 135407194, compound

Procedure

A mixture of the pyridobenzimidazo derivative VII prepared as in Example 1 (3.5 g, 13.6 mM) and phenol (7.0 g, 74.5 mM) in xylenes (350 mL) was heated to reflux under argon for 6 h and left at room temperature for 16 h. The resulting solid precipitate was filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by HPLC, using methylene chloride and THF as eluents followed by recrystallization of the desired fractions from methylene chloride and acetone to give the title compound as a solid: mp 176-178° C.; MS: 307 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under argon for 6 h
  3. filtrationThe resulting solid precipitate was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe resulting residue was purified by HPLC
  6. customfollowed by recrystallization of the desired fractions from methylene chloride and acetone

Sources & evidence

ORD record
ord-b488cdfc2fa3410682062a015925e205
Source dataset
uspto-grants-2001_04
Patent number
US06218384B1

Reaction notes

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