Hydrogen chloride-ethyl acetate → HCID 86724014, compound

HRID 1475421Notes

Reaction equation

HRID 1475421 reaction equation
C(OC([N:8]1[C:16]2[CH:15]=[C:14]([Cl:17])[N:13]=[N:12][C:11]=2[C:10]([CH3:19])([CH3:18])[CH2:9]1)=O)(C)(C)C.Cl.CCOC(C)=O>CCOC(C)=O>[Cl:17][C:14]1[N:13]=[N:12][C:11]2[C:10]([CH3:19])([CH3:18])[CH2:9][NH:8][C:16]=2[CH:15]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86724013HCID 86724013, compound

Product 1

HCID 86724014HCID 86724014, compoundYield 125.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Chloro-7,7-dimethyl-6,7-dihydro-pyrrolo[3,2-c]pyridazine-5-carboxylic acid tert-butyl ester (75 mg) suspended in EtOAc (0.5 mL) was stirred under a N2 atmosphere. 4M HCl/EtOAc (5 mL) was added slowly and after complete addition the mixture was stirred for 8 h. LC analysis indicated 10% starting material remaining. The reaction mixture was concentrated in vacuo and the following morning taken up in 4M HCl/EtOAc (5 mL). The solution was stirred for 1 h after which point LC analysis indicated complete consumption of the starting material. The reaction mixture was concentrated in vacuo and azeotroped with MeOH (2×5 mL) to provide the title compound (61 mg) as a white solid. 1H NMR (270 MHz, D4-MeOH): 6.92 (1H, s), 3.79 (2H, s) and 1.44 (6H, s). MS: [M+H]+=184.

Workup

  1. additionafter complete addition the mixture
  2. stirringwas stirred for 8 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. stirringThe solution was stirred for 1 h after which point LC analysis
  5. customconsumption of the starting material
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. customazeotroped with MeOH (2×5 mL)

Sources & evidence

ORD record
ord-188e40eb5e4e4dbdb4a0eb980dfdd0b5
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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