Hydrochloric Acid → HCID 19081386, compound

HRID 963204Notes

Reaction equation

HRID 963204 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[C:9](=[O:26])[N:10]([C:22]([CH3:25])([CH3:24])[CH3:23])[N:11]=[CH:12][C:13]=1[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.[C:27]1([S:33](Cl)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>C(Cl)Cl.O>[C:27]1([S:33]([NH:7][C:8]2[C:9](=[O:26])[N:10]([C:22]([CH3:23])([CH3:25])[CH3:24])[N:11]=[CH:12][C:13]=2[NH:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 19081395HCID 19081395, compound

Product 1

HCID 19081386HCID 19081386, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Into 6 ml of a pyridine solution of 0.55 g of 4-amino-2-tert-butyl-5-(4-pyridylmethylamino)pyridazin-3-(2H)-one, 0.36 g of benzenesulfonyl chloride was dropwise added at room temperature. The mixture was reacted overnight, and 80 ml of water and 100 ml of methylene chloride were added to the system. The mixture was adjusted to pH4 with dilute hydrochloric acid under cooling with ice, and then stirred for 20 minutes. The organic layer was dried over anhydrous sodium sulfate and then concentrated. To the residue, 4 ml of ethyl acetate was added, and the mixture was mashed, whereupon crystals were collected by filtration. The obtained crystals were subjected to column chromatography, and using an eluent (n-hexane:ethyl acetate=1:5), 0.30 g of the desired product (Compound No. 32) having a melting point of from 189° to 190° C., was obtained.

Workup

  1. customThe mixture was reacted overnight
  2. temperatureunder cooling with ice
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. additionTo the residue, 4 ml of ethyl acetate was added
  6. filtrationwere collected by filtration
  7. customof from 189° to 190° C.
  8. customwas obtained

Sources & evidence

ORD record
ord-28d6ad1e07994c7aa5fe7e8338db336e
Source dataset
uspto-grants-1998_06
Patent number
US05763439

Reaction notes

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