Sodium Hydroxide → HCID 67011554, compound

HRID 2111789Notes

Reaction equation

HRID 2111789 reaction equation
[OH-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][NH:10][C:11]([C:13]2[CH:41]=[CH:40][C:16]3[N:17]([C:20]4[CH:39]=[CH:38][C:23]([O:24][CH2:25][CH2:26][O:27][C:28]5[CH:29]=[N:30][CH:31]=[C:32]([CH:37]=5)[C:33]([O:35]C)=[O:34])=[CH:22][CH:21]=4)[CH:18]=[N:19][C:15]=3[CH:14]=2)=[O:12])[CH:4]=1.OC1C=NC=C(C=1)C(OC)=O>CO>[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][NH:10][C:11]([C:13]2[CH:41]=[CH:40][C:16]3[N:17]([C:20]4[CH:39]=[CH:38][C:23]([O:24][CH2:25][CH2:26][O:27][C:28]5[CH:29]=[N:30][CH:31]=[C:32]([CH:37]=5)[C:33]([OH:35])=[O:34])=[CH:22][CH:21]=4)[CH:18]=[N:19][C:15]=3[CH:14]=2)=[O:12])[CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 354317Methyl 5-hydroxypyridine-3-carboxylateHCID 69069155HCID 69069155, compound

Product 1

HCID 67011554HCID 67011554, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution of sodium hydroxide (0.107 mmol, 43 μL, 100 mg/mL) was added to methyl 5-(2-{4-[5-(pyridin-3-ylmethylaminocarbonyl)-1H-benzimidazol-1-yl]phenoxy}ethoxy)nicotinate (prepared according to the procedure described above utilising methyl 5-hydroxynicotinate in place of 3-hydroxypyridine, 37 mg, 0.07 mmol) in methanol and the mixture heated at reflux for 18 h. The mixture was then concentrated in vacuo and purified by preparative HPLC to yield the title compound. 1H NMR (d6-DMSO, 400 MHz): δ 9.15 (t, J=6.0 Hz, 1H), 8.64 (s, 1H), 8.60-8.50 (m, 2H), 8.40-8.39 (m, 2H), 8.38 (d, J=1.6 Hz, 1H), 8.35 (s, 1H), 7.87 (dd, J=8.4, 1.6 Hz, 1H), 7.78 (s, 1H), 7.73 (d, J=7.6 Hz, 1H), 7.59 (dd, J=12.4, 8.8 Hz, 3H), 7.35 (dd, J=7.6, 5.2 Hz, 1H), 7.23 (d, J=8.8 Hz, 2H), 4.51 (d, J=6.0 Hz, 2H), 4.50-4.4 (m, 4H); MS (ES+): m/z 510 [MH+], 511 [MH+2].

Workup

  1. customprepared
  2. temperaturethe mixture heated
  3. temperatureat reflux for 18 h
  4. concentrationThe mixture was then concentrated in vacuo
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-adc09da3813e4bb28763702857084897
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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