Hydrochloric Acid → 3-(3-(4-Chloro-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)benzylthio)benzoic acid

HRID 625269Notes

Reaction equation

HRID 625269 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:28][C:29](=[O:38])[C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36]Cl)[CH:31]=2)=[C:6]([C:8]2[CH:9]=[C:10]([CH:25]=[CH:26][N:27]=2)[C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[O:12])[CH:7]=1.ClCC1C=C(C=CC=1)C(NC1C=CC(N2CCCCC2)=CC=1C1C=C(C=CN=1)C(NCC1C=CC=C(C(F)(F)F)C=1)=O)=O.[SH:82][C:83]1[CH:84]=[C:85]([CH:89]=[CH:90][CH:91]=1)[C:86]([OH:88])=[O:87].C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:28][C:29]([C:30]2[CH:31]=[C:32]([CH:33]=[CH:34][CH:35]=2)[CH2:36][S:82][C:83]2[CH:84]=[C:85]([CH:89]=[CH:90][CH:91]=2)[C:86]([OH:88])=[O:87])=[O:38])=[C:6]([C:8]2[CH:9]=[C:10]([C:11](=[O:12])[NH:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:22])[F:24])[CH:16]=3)[CH:25]=[CH:26][N:27]=2)[CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 95737Benzoic acid, 3-mercapto-HCID 665867362-(2-(3-(chloromethyl)benzamido)-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)benzyl)-isonicotinamideHCID 665868092-(5-chloro-2-(3-(chloromethyl)benzamido)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide

Product 1

HCID 675121873-(3-(4-Chloro-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)benzylthio)benzoic acidYield 43.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 173 mg of 2-(5-chloro-2-(3-(chloromethyl)benzamido)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide, which was made from intermediate 21b in a similar manner as the synthesis of 8.1a, 52 mg of 3-mercaptobenzoic acid, and 128 mg of K2CO3 in 2 mL of DMF was stirred for 2 h and then poured into 20 mL of water. The solution was acidified with hydrochloric acid. A precipitate formed and was collected by filtration and dried. The resulting solid was dissolved in acetone and filtered. Evaporation of the solvent gave 92 mg of product. MS (ES, m/z) 676 [M+H]+.

Workup

  1. customA precipitate formed
  2. filtrationwas collected by filtration
  3. customdried
  4. dissolutionThe resulting solid was dissolved in acetone
  5. filtrationfiltered
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-0ed73f7494e4493998b80573c2a6f71c
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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