Hydrochloric Acid → HCID 86717475, compound

HRID 712017Notes

Reaction equation

HRID 712017 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([NH:11][C:12]3[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][N:15]=[C:14]4[CH:21]=[CH:22][S:23][C:13]=34)[CH2:7][CH2:6]2)[O:4]CC1.Cl.O.[OH-].[Na+]>CC(C)=O>[N+:18]([C:17]1[C:12]([NH:11][CH:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)=[C:13]2[S:23][CH:22]=[CH:21][C:14]2=[N:15][CH:16]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86717474HCID 86717474, compound

Product 1

HCID 86717475HCID 86717475, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-1,4-dioxaspiro[4.5]dec-8-yl-6-nitrothieno[3,2-b]pyridin-7-amine (0.45 g, 1.3 mmol) and 3.0 M hydrogen chloride in water (9 mL, 30 mmol) in acetone (20 mL) was stirred at room temperature for 20 min and then at 60° C. for 1 h. The mixture was basified with aq. 5M NaOH solution at 0° C., then extracted with EtOAc. The combined organic layers were dried over sodium sulfate, concentrated and purified on silica gel column (eluting with 0-30% of EtOAc in methylene chloride) to give the desired product (0.2 g, 51% in 2 steps). LCMS calculated for C13H14N3O3S (M+H)+: m/z=292.1. Found: 292.0.

Workup

  1. waitat 60° C. for 1 h
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified on silica gel column (eluting with 0-30% of EtOAc in methylene chloride)

Sources & evidence

ORD record
ord-380f4a267e584b129781190a94b6be14
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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