4-(3-(Trifluoromethyl)phenyl)-1-piperazineethanol → 2-[4-(3-Trifluoromethylphenyl)-piperazin-1-yl]-ethyl 2-(7-chloro-4-quinolinylamino)-5-fluoro-benzoate

HRID 224589Notes

Reaction equation

HRID 224589 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:14]=3[C:15]([O:17][CH3:18])=[O:16])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[F:24][C:25]([F:42])([F:41])[C:26]1[CH:27]=[C:28]([N:32]2[CH2:37][CH2:36][N:35]([CH2:38]CO)[CH2:34][CH2:33]2)[CH:29]=[CH:30][CH:31]=1>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:14]=3[C:15]([O:17][CH2:18][CH2:38][N:35]3[CH2:34][CH2:33][N:32]([C:28]4[CH:29]=[CH:30][CH:31]=[C:26]([C:25]([F:42])([F:24])[F:41])[CH:27]=4)[CH2:37][CH2:36]3)=[O:16])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2179944-(3-(Trifluoromethyl)phenyl)-1-piperazineethanolHCID 23331682Methyl 2-(7-chloro-4-quinolinylamino)-5-fluoro-benzoate

Product 1

HCID 233316982-[4-(3-Trifluoromethylphenyl)-piperazin-1-yl]-ethyl 2-(7-chloro-4-quinolinylamino)-5-fluoro-benzoateYield 6.1%

Procedure

Using the procedure of Example 3, 4 g of the ester of Example 1 and 3.316 g of 2-[4-(3-trifluoromethylphenyl)-piperazin-1-yl]-ethanol were reacted to obtain 6.88 g of a raw oily product. 500 mg of the said product were crystallized from isopropyl ether to obtain 425 mg of 2-[4-(3-trifluoromethylphenyl)-piperazin-1-yl]-ethyl 2-(7-chloro-4-quinolinylamino)-5-fluoro-benzoate melting at 113° C.

Workup

  1. customwere reacted
  2. customto obtain 6.88 g of a raw oily product
  3. custom500 mg of the said product were crystallized from isopropyl ether

Sources & evidence

ORD record
ord-fdf542fb226c4ba39f34b482f3210ff5
Source dataset
uspto-grants-1980_11
Patent number
US04233305

Reaction notes

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