Dichloromethane → HCID 86683167, compound

HRID 920949Notes

Reaction equation

HRID 920949 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:15][C:16]1[C:21]2[C:22](=[O:26])[NH:23][N:24]=[CH:25][C:20]=2[CH:19]=[N:18][CH:17]=1.[N:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][C:28]=1[CH2:37][CH2:38]O.C(Cl)Cl>C1COCC1.O>[Cl:15][C:16]1[C:21]2[C:22](=[O:26])[N:23]([CH2:38][CH2:37][C:28]3[CH:29]=[CH:30][C:31]4[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=4)[N:27]=3)[N:24]=[CH:25][C:20]=2[CH:19]=[N:18][CH:17]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 705322-QuinolineethanolHCID 5363146Diisopropyl azodicarboxylateHCID 86683166HCID 86683166, compound

Product 1

HCID 86683167HCID 86683167, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent5×

Procedure

To 69.3 mg (0.264 mmol) in THF was added diisopropylazodicarboxylate (94 mg, 0.463 mmol) in THF under ice-cooling and under nitrogen. Then, the resulting solution was stirred for 30 min at room temperature to give a suspension. 8-Chloropyrido[4,3-d]pyridazin-1(2H)-one (24 mg, 0.132 mmol) in THF and then 2-(quinolin-2-yl)ethanol (22.89 mg, 0.132 mmol) in THF were added and the reaction mixture was stirred overnight at room temperature. The total amount of THF was 60 mL. Then, the reaction mixture was mixed with DCM and water. The organic phase was washed with 1N HCl and the organic phase was discharged. The aqueous phase was basified by 1N NaOH and extracted with DCM. The organic phase was dried and concentrated to give 34 mg (76%) of the title compound as bright beige solid. LC-MS: m/e 337.1 (M+H)+.

Workup

  1. temperaturecooling and under nitrogen
  2. customto give a suspension
  3. stirringthe reaction mixture was stirred overnight at room temperature
  4. washThe organic phase was washed with 1N HCl
  5. extractionextracted with DCM
  6. customThe organic phase was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a0a766383f394fe3b2f066db993f536e
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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