Hydrochloric Acid → HCID 178478950, compound

HRID 1518147Notes

Reaction equation

HRID 1518147 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:26]=[CH:25][C:11]2[NH:12][C:13]([C:15]3[CH2:19][C:18]4([CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[O:17][N:16]=3)=[N:14][C:10]=2[CH:9]=1.[ClH:27]>CCO>[ClH:27].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:26]=[CH:25][C:11]2[NH:12][C:13]([C:15]3[CH2:19][C:18]4([CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)[O:17][N:16]=3)=[N:14][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1785056043-[5-(2-Fluoro-phenyl)-1H-benzimidazol-2-yl]-1,8-dioxa-2-aza-spiro[4.5]dec-2-ene

Product 1

HCID 178478950HCID 178478950, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-[5-(2-fluoro-phenyl)-1H-benzimidazol-2-yl]-1,8-dioxa-2-aza-spiro[4.5]dec-2-ene (98.8 mg, 0.281 mmol, as prepared in the previous step) in EtOH (5 mL) was treated with HCl (56.2 μL, 0.281 mmol, 5 M in isopropanol) at rt for 2 h. The mixture was concentrated in vacuo and the residue was dissolved in a minimum amount of EtOH (2.5 mL) with sonication and heating. The solution was cooled to rt, and hexanes were added dropwise until the solution became cloudy. The solution was allowed to sit for 2 min then was treated with additional hexanes. The resulting precipitate was filtered, washed with hexanes, and air-dried to afford the title compound (63.7 mg, 58%) as a white solid. 1H-NMR (400 MHz, d4-MeOH) δ: 7.85 (s, 1H), 7.77-7.83 (m, 1H), 7.70-7.77 (m, 1H), 7.46-7.53 (m, 1H), 7.32-7.41 (m, 1H), 7.21-7.27 (m, 1H), 7.13-7.21 (m, 1H), 3.78-3.88 (m, 2H), 3.63-3.73 (m, 2H), 3.32-3.36 (m, 2H), 1.85-1.98 (m, 4H). Mass Spectrum (LCMS, APCI pos.): Calcd. for C20H18FN3O2: 352.1 (M+H). found: 352.3.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in a minimum amount of EtOH (2.5 mL) with sonication
  3. temperatureheating
  4. additionhexanes were added dropwise until the solution
  5. additionthen was treated with additional hexanes
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with hexanes
  8. customair-dried

Sources & evidence

ORD record
ord-caa5ad6e28bb4ad29447fbcebee1d097
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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