1,2,3,4-Tetrahydroquinoline → 3-Methoxy-6-(tetrahydroquinoline-1-sulfonyl)-pyridazine

HRID 22756

Reaction equation

HRID 22756 reaction equation
[N:1]1([S:11]([C:14]2[N:15]=[N:16][CH:17]=[CH:18][CH:19]=2)(=[O:13])=[O:12])[C:10]2[CH:5]([CH2:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.FS(C1N=N[C:27]([O:30]C)=CC=1)(=O)=O.N1C2C(=CC=CC=2)CCC1>>[CH3:27][O:30][C:17]1[N:16]=[N:15][C:14]([S:11]([N:1]2[C:10]3[CH:5]([CH2:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)(=[O:13])=[O:12])=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 694601,2,3,4-TetrahydroquinolineHCID 110306363-Fluorosulfonyl-6-methoxypyridazineHCID 86589093Tetrahydroquinoline-1-sulfonyl-pyridazine

Product 1

HCID 690499883-Methoxy-6-(tetrahydroquinoline-1-sulfonyl)-pyridazineYield 73%

Conditions

Temperature
140 °C

Procedure

3-Methoxy-6-(tetrahydroquinoline-1-sulfonyl-pyridazine. A mixture of 3-fluorosulfonyl-6-methoxypyridazine (2 mmol, 384 mg) and tetrahydroquinoline (4 mmol, 532 mg) was heated at 140° C. for two hours. The reaction mixture was cooled, extracted with EtOAc (20 mL), and the EtOAc extract was dried, filtered and evaporated to obtain 3-methoxy-6-(tetrahydroquinoline-1-sulfonyl)-pyridazine (73%, 451 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc (20 mL)
  3. extractionthe EtOAc extract
  4. customwas dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-676384e4c29d4a74a0018de6aa100369
Source dataset
uspto-grants-2005_02
Patent number
US06849629B2

Linked notes

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