HCID 23331704, compound → HCID 23331696, compound

HRID 224590Notes

Reaction equation

HRID 224590 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH:15](O)[CH3:16])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[F:20][C:21]([F:45])([F:44])[C:22]1[CH:31]=[C:30]2[C:25]([C:26]([NH:32][C:33]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:34]=3[C:35]([O:37]C)=[O:36])=[CH:27][CH:28]=[N:29]2)=[CH:24][CH:23]=1>>[F:45][C:21]([F:20])([F:44])[C:22]1[CH:31]=[C:30]2[C:25]([C:26]([NH:32][C:33]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:34]=3[C:35]([O:37][CH2:16][CH2:15][N:12]3[CH2:13][CH2:14][N:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:19])([F:18])[F:1])[CH:4]=4)[CH2:10][CH2:11]3)=[O:36])=[CH:27][CH:28]=[N:29]2)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 23331704HCID 23331704, compoundHCID 23331707HCID 23331707, compound

Product 1

HCID 23331696HCID 23331696, compoundYield 76.8%

Procedure

Using the procedure of Step B of Example 7, 6.57 g of 4-(3-trifluoromethylphenyl)-piperazin-1-yl-ethanol and 9.19 g of methyl 2-(7-trifluoromethyl-4-quinolinylamino)-5-fluoro-benzoate were reacted to obtain 12.72 g of raw product which was chromatographed over silica gel. Elution with 95-5 methylene chloride-methanol mixture yielded 11.16 g of 2-[4-(3-trifluoromethylphenyl)-piperazin-1-yl]-ethyl 2-(7-trifluoromethyl-4-quinolinylamino)-5-fluoro-benzoate. The said product was dissolved in 25 ml of hot absolute ethanol and then 5.6 ml of an ethanol solution of 6.6 N hydrochloric acid was added thereto at 50° C. The mixture was stirred and 60 ml of anhydrous ether were added thereto in small amounts. The mixture was stirred overnight at room temperature and after the addition of 0.5 ml of the ethanolic hydrochloric acid solution, the mixture was stirred for one hour and was vacuum filtered. The recovered crystals were washed with a 1-3 anhydrous ethanol-ether mixture and then with ether to obtain 11.7 g of the dihydrochloride of 2-[4-(3-trifluoromethylphenyl)-piperazin-1-yl]-ethyl 2-(7-trifluoromethyl-4-quinolinylamino)-5-fluoro-benzoate melting at 200° C.

Workup

  1. customwere reacted
  2. customto obtain 12.72 g of raw product which
  3. customwas chromatographed over silica gel
  4. washElution with 95-5 methylene chloride-methanol mixture

Sources & evidence

ORD record
ord-98a1f47aba3846ad91df42f5a2935034
Source dataset
uspto-grants-1980_11
Patent number
US04233305

Reaction notes

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