Hydrochloric Acid → HCID 135923533, compound

HRID 2076822Notes

Reaction equation

HRID 2076822 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][O:10][CH2:11][C:12]([NH:14][C:15]([C:17]2[CH:22]=[C:21]([Cl:23])[N:20]=[N:19][C:18]=2Cl)=[O:16])=[NH:13])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].O.Cl>CN(C=O)C>[Cl:23][C:21]1[N:20]=[N:19][C:18]2[N:13]=[C:12]([CH2:11][O:10][CH2:9][CH2:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[NH:14][C:15](=[O:16])[C:17]=2[CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 141215262HCID 141215262, compound

Product 1

HCID 135923533HCID 135923533, compoundYield 0.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of crude 3,6-dichloro-pyridazine-4-carboxylic acid{2-[2-(3-chloro-phenyl)-ethoxy]-1-imino-ethyl}-amide (170 mg) and K2CO3 (121 mg, 0.877 mmol) in DMF (2 ml) was heated to 100° C. for 2 h. Then water was added and the pH was adjusted to 2 by addition of 0.1 N HCl. The resulting mixture was extracted two times with CH2Cl2 and the combined extracts were washed with water and brine, dried (Na2SO4) and evaporated. The remaining residue was purified by column chromatography (silica gel, CH2Cl2/MeOH 100:0 to 98:2) to give the title compound as light yellow solid (1 mg, 0.5%). MS: m/e=351.1 [M+H+].

Workup

  1. extractionThe resulting mixture was extracted two times with CH2Cl2
  2. washthe combined extracts were washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe remaining residue was purified by column chromatography (silica gel, CH2Cl2/MeOH 100:0 to 98:2)

Sources & evidence

ORD record
ord-17ae7eda993d4559a3a378471979cbba
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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