Sodium Hydroxide → HCID 19008909, compound

HRID 1742431Notes

Reaction equation

HRID 1742431 reaction equation
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[N:20]2[C:24]3=[N:25][CH:26]=[CH:27][CH:28]=[C:23]3[N:22]=[C:21]2[CH2:29][CH2:30][CH2:31][CH3:32])[CH:11]=1.[OH-].[Na+]>CCO>[CH2:29]([C:21]1[N:20]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:17]=2[CH:18]=[CH:19][C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([OH:33])=[O:2])=[CH:11]3)[C:24]2=[N:25][CH:26]=[CH:27][CH:28]=[C:23]2[N:22]=1)[CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54282996HCID 54282996, compound

Product 1

HCID 19008909HCID 19008909, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-[5-(2-butyl-imidazo[4,5-b]pyridin-3-yl)-naphthalen-2-yl]-benzoic acid methyl ester (40 mg) in EtOH (1.0 mL) at room temperature was added 2N NaOH (0.5 mL). The reaction mixture was heated at 50° C. for 17 hours. The cooled solution was concentrated in vacuo. The residue was diluted with saturated aqueous NaCl (10 mL) and neutralized with concentrated HOAc. The aqueous solution was extracted with CHCl3 (3×30 mL). The combined extracts were dried MgSO4) and concentrated in vacuo. The residue was azeotroped with heptane (30 mL) and diluted with EtOAc (1 mL) and hexanes (15 mL). The solid that precipitated was filtered and dried. 1H NMR (250 MHz, d6 -DMSO): d 8.15 (m, 4 H), 7.72 (m, 3 H), 7.46 (m, 4 H), 7.30 (dd, 1 H), 6.94 (d, 1 H), 2.63 (m, 2 H), 1.63 (m, 2 H), 1.25 (m, 2 H), 0.74 (t, 3 H).

Workup

  1. concentrationThe cooled solution was concentrated in vacuo
  2. additionThe residue was diluted with saturated aqueous NaCl (10 mL) and neutralized with concentrated HOAc
  3. extractionThe aqueous solution was extracted with CHCl3 (3×30 mL)
  4. concentrationconcentrated in vacuo
  5. customThe residue was azeotroped with heptane (30 mL)
  6. additiondiluted with EtOAc (1 mL) and hexanes (15 mL)
  7. customThe solid that precipitated
  8. filtrationwas filtered
  9. customdried

Sources & evidence

ORD record
ord-4f63c666d08c4fc19d053872c6a2c86d
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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