HCID 14726219, compound → HCID 14726454, compound

HRID 1087156Notes

Reaction equation

HRID 1087156 reaction equation
C([N:5]1[C:10](=[O:11])[C:9]([NH:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[CH2:17][CH2:16]2)=[C:8]([Cl:31])[CH:7]=[N:6]1)(C)(C)C>Cl>[Cl:31][C:8]1[CH:7]=[N:6][NH:5][C:10](=[O:11])[C:9]=1[NH:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][N:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=2)[CH2:19][CH2:20]1

Participants

3

Reactant 1

HCID 14726219HCID 14726219, compound

Product 1

HCID 14726454HCID 14726454, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4.25 g (0.0093 mol) of 2-t-butyl-5-chloro-4-((2(4-(3-trifluoromethylphenyl)-1-piperazinyl)ethyl)amino)-3(2H)-pyridazinone are stirred with 50 ml of concentrated aqueous hydrochloric acid at room temperature for 72 hours, made basic and extracted 3 times with chloroform, 10 the organic phase is concentrated and dried with sodium sulphate, and the residue is triturated with acetone. The crystalline precipitate of 5-chloro-4-((2-(4-(3-trifluoromethylphenyl)-1-piperazinyl)ethyl)amino)-3(2H)-pyridazinone weighs 2.40 g (47.7% of theory). It is converted by dissolving in 100 ml of hot absolute ethanol and adding ethereal hydrochloric acid into 2.20 g (46.7% of theory) of dihydrochloride of m.p. 220°-223° C.; C 40.6%, H 4.2%, Cl(tot) 21.1%, Cl- 14.2%, F 11.5%, N 13.9%, O 8.7%, UV in 0.1N HCl: 208(4.42), 226(S,4.22), 300(4.47).

Workup

  1. extractionextracted 3 times with chloroform, 10 the organic phase
  2. concentrationis concentrated
  3. dry with materialdried with sodium sulphate
  4. customthe residue is triturated with acetone
  5. dissolutionby dissolving in 100 ml of hot absolute ethanol
  6. additionadding ethereal hydrochloric acid into 2.20 g (46.7% of theory) of dihydrochloride of m.p. 220°-223° C.

Sources & evidence

ORD record
ord-9b74a2b4f94940e9b8ca4c96b10eb2b8
Source dataset
uspto-grants-1991_07
Patent number
US05034391

Reaction notes

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