Methanol → 4-Chloro-3-cyano-5-methoxymethyl-pyrrolo[1,2-b]pyridazine-6-carboxylic Acid Ethyl Ester

HRID 2183482Notes

Reaction equation

HRID 2183482 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:18]Br)=[C:8]2[C:13]([Cl:14])=[C:12]([C:15]#[N:16])[CH:11]=[N:10][N:9]2[CH:17]=1)=[O:5])[CH3:2].CO.[C:22]([O-])(O)=[O:23].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:18][O:23][CH3:22])=[C:8]2[C:13]([Cl:14])=[C:12]([C:15]#[N:16])[CH:11]=[N:10][N:9]2[CH:17]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 207916315-Bromomethyl-4-chloro-3-cyano-pyrrolo[1,2-b]pyridazine-6-carboxylic Acid Ethyl Ester

Product 1

HCID 207916284-Chloro-3-cyano-5-methoxymethyl-pyrrolo[1,2-b]pyridazine-6-carboxylic Acid Ethyl EsterYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of compound 16A (31 mg, 0.09 mmol) in 1:1 MeOH:CH2Cl2 (2 mL) was added NaHCO3 (30 mg, 0.36 mmol). The reaction was kept at room temperature for 3 h, heated to 70° C. for 1 h, cooled to room temperature, concentrated to dryness, redissolved in CH2Cl2 and filtered. The filtrate was concentrated to give compound 17A as a yellow solid (26 mg, 98%).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated to dryness
  3. dissolutionredissolved in CH2Cl2
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-879141e1d5bb483f970ee6f13b75835a
Source dataset
uspto-grants-2005_05
Patent number
US06900208B2

Reaction notes

Loading…