Hydrochloric Acid → HCID 86717563, compound

HRID 712111Notes

Reaction equation

HRID 712111 reaction equation
[N:1]1([C:13]2([CH2:23][OH:24])[CH2:22][CH2:21][C:16]3(OCC[O:17]3)[CH2:15][CH2:14]2)[C:5]2=[C:6]3[S:12][CH:11]=[CH:10][C:7]3=[N:8][CH:9]=[C:4]2[N:3]=[CH:2]1.Cl.O.[OH-].[Na+]>CC(C)=O>[OH:24][CH2:23][C:13]1([N:1]2[C:5]3=[C:6]4[S:12][CH:11]=[CH:10][C:7]4=[N:8][CH:9]=[C:4]3[N:3]=[CH:2]2)[CH2:22][CH2:21][C:16](=[O:17])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86717561HCID 86717561, compound

Product 1

HCID 86717563HCID 86717563, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of [8-(1H-imidazo[4,5-d]thieno[3,2-b]pyridin-1-yl)-1,4-dioxaspiro[4.5]dec-8-yl]methanol (0.13 g, 0.38 mmol) and 3.0 M hydrogen chloride in water (2.0 mL, 6.0 mmol) in acetone (5 mL) was stirred at room temperature for 5 h and then at 60° C. for 1 h. After cooling, the mixture was made slightly basic by the addition of 2.0 N NaOH. The mixture was extracted with EtOAc (3×). The combined extracts were dried (Na2SO4), filtered, and concentrated. The crude was purified on silica gel, eluted with 0-15% MeOH in dichloromethane to give 56 mg (49%) of the desired product. LCMS calculated for C15H16N3O2S (M+H)+: m/z=302.1. Found: 302.1.

Workup

  1. waitat 60° C. for 1 h
  2. temperatureAfter cooling
  3. extractionThe mixture was extracted with EtOAc (3×)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified on silica gel
  8. washeluted with 0-15% MeOH in dichloromethane

Sources & evidence

ORD record
ord-44255885484c4213bc9f19722a8a09d3
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

Loading…