4,7-Dichloroquinoline → HCID 21399771, compound

HRID 1439123Notes

Reaction equation

ClC1C=C2C(C(NC3C=CC(C(N4CCN(C)CC4)=[O:18])=CC=3)=CC=N2)=CC=1.[Cl:28][C:29]1[CH:38]=[C:37]2[C:32]([C:33]([NH:39][C:40]3[CH:60]=[CH:59][C:43]([C:44]([N:46]4[CH2:51][CH2:50][N:49]([C:52]5[CH:57]=[CH:56][C:55](Cl)=[CH:54][CH:53]=5)[CH2:48][CH2:47]4)=[O:45])=[CH:42][CH:41]=3)=[CH:34][CH:35]=[N:36]2)=[CH:31][CH:30]=1.ClC1C=C2C(C(NC3C=CC(C(N4CCN(C5C=CC=C(OC)C=5)CC4)=O)=CC=3)=CC=N2)=CC=1.ClC1C=C2C(C(NC3C=CC(C(N4CCN(C5C=CC=C(C(F)(F)F)C=5)CC4)=O)=CC=3)=CC=N2)=CC=1.ClC1C2C(=CC(Cl)=CC=2)N=CC=1.NC1C=CC(C(N)=O)=CC=1>>[Cl:28][C:29]1[CH:38]=[C:37]2[C:32]([C:33]([NH:39][C:40]3[CH:60]=[CH:59][C:43]([C:44]([N:46]4[CH2:51][CH2:50][N+:49]([O-:18])([C:52]5[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=5)[CH2:48][CH2:47]4)=[O:45])=[CH:42][CH:41]=3)=[CH:34][CH:35]=[N:36]2)=[CH:31][CH:30]=1

Participants

Reactant 6

HCID 68664,7-Dichloroquinoline

HCID 760794-Aminobenzamide

HCID 10362407Piperazine, 1-[4-[(7-chloro-4-quinolinyl)amino]benzoyl]-4-methyl-

HCID 21399760HCID 21399760, compound

HCID 21399774HCID 21399774, compound

HCID 21399780HCID 21399780, compound

Product 1

HCID 21399771HCID 21399771, compound

Procedure

Similary, following the procedure of Example 1 above but replacing the 1-[p-[(7-chloro-4-quinolyl)amino]benzoyl]-4-methylpiperazine as used therein with 1-[p-[(7-chloro-4-quinolyl)amino]benzoly]-4-phenylpiperazine; 1-[p-[(7-chloro-4-quinolyl)amino]benzoyl]-4-(p-chlorophenyl)piperazine; 1-[p-[(7-chloro-4-quinolyl)amino]benzoyl]-4(m-methoxyphenyl)piperazine; 1-[p-[(7-chloro-4-quinolyl)amino]benzoly]-4-(o-tolyl)piperazine; and 1-[p-[(7-chloro-4-quinolyl)amino]-benzoyl]-4-(m-trifluoromethylphenyl)piperazine, respectively, all of which may be prepared by reacting 4,7-dichloroquinoline with an appropriate p-aminobenzamide of formula (IV), supra. according to the method of Morley et al., supra., there is obtained the corresponding 1-[p-[(7-chloro-4-quinolyl)amino]benzoyl]-4-phenylpiperazine-4-oxide; 1-[p-[(7-chloro-4-quniolyl)amino]benzoly]-4-chlorophenyl)-piperazine-4-oxide; 1-[p-[(7-chloro-4-quinolyl)amino]benzoyl]-4-(m-methoxyphenyl)piperazine-4-oxide; 1-[p-[(7-chloro-4-quinolyl)amino]benzoyl]-4-(o-tolyl)piperazine-4-oxide; and 1-[p-[(7-chloro-4 -quinolyl)amino]benzoyl]-4-(m-trifluoromethylphenyl)piperazine-4-oxide, respectively.

Sources & evidence

ORD record: ord-a87c95c60b8442098ff2075a004203e4
Source dataset: uspto-grants-1977_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04057633

Reaction notes

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