3-Chlorobenzenesulphonyl chloride → HCID 86611326, compound

HRID 2235155Notes

Reaction equation

HRID 2235155 reaction equation
N1C2C(=CC=C(C(O)=O)C=2)C=CC=1.NC1C=CC(C#N)=C(C(F)(F)F)C=1.[C:27]([C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36]([C:38]2[CH:47]=[C:46]3[C:41]([CH:42]=[CH:43][CH:44]=[N:45]3)=[CH:40][CH:39]=2)=[O:37])=[CH:31][C:30]=1[C:48]([F:51])([F:50])[F:49])#[N:28].C(C1C=CC(NC(C2C=C3C(CCCN3)=CC=2)=O)=CC=1C(F)(F)F)#N.[Cl:77][C:78]1[CH:79]=[C:80]([S:84](Cl)(=[O:86])=[O:85])[CH:81]=[CH:82][CH:83]=1>>[C:27]([C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36]([C:38]2[CH:47]=[C:46]3[C:41]([CH2:42][CH2:43][CH2:44][N:45]3[S:84]([C:80]3[CH:81]=[CH:82][CH:83]=[C:78]([Cl:77])[CH:79]=3)(=[O:86])=[O:85])=[CH:40][CH:39]=2)=[O:37])=[CH:31][C:30]=1[C:48]([F:51])([F:49])[F:50])#[N:28]

Participants

6

Reactant 5

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 5221704-Amino-2-(trifluoromethyl)benzonitrileHCID 599475Quinoline-7-carboxylic acidHCID 86100645HCID 86100645, compoundHCID 86611327HCID 86611327, compound

Product 1

HCID 86611326HCID 86611326, compound

Procedure

In analogy to example 40, quinoline-7-carboxylic acid was reacted with 4-amino-2-trifluoromethyl-benzonitrile in step 2, and the resulting quinoline-7-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide was reduced to 1,2,3,4-tetrahydro-quinoline-7-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide in step 3. This was coupled with 3-chloro-benzenesulfonyl chloride in step 4, yielding 1-(3-chloro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide.

Sources & evidence

ORD record
ord-9be8a24bf25448159407bc8d3eff6841
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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