4-Nitrobenzoic Acid → HCID 66877345, compound

HRID 633182Notes

Reaction equation

HRID 633182 reaction equation
ClC1C=CC(N)=CC=1C1C=CC=CN=1.[N+](C1C=CC(C(O)=O)=CC=1)([O-])=O.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:45])[C:36]2[CH:41]=[CH:40][C:39]([N+:42]([O-])=O)=[CH:38][CH:37]=2)=[CH:30][C:29]=1[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=1.[Sn](Cl)Cl>Cl.CCO>[NH2:42][C:39]1[CH:40]=[CH:41][C:36]([C:35]([NH:34][C:31]2[CH:32]=[CH:33][C:28]([Cl:27])=[C:29]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=3)[CH:30]=2)=[O:45])=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 24479Stannous ChlorideHCID 401519254-Chloro-3-(pyridin-2-yl)anilineHCID 66878156HCID 66878156, compound

Product 1

HCID 66877345HCID 66877345, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

300 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 270 mg of 4-nitrobenzoic acid via Procedure G. To 520 mg of N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-nitrobenzamide in 2.5 mL of HCl in 10 mL of EtOH was added 1.3 g of Tin (II) Chloride and stirred at 55° C. Upon completion, the reaction was concentrated and extracted with Ethyl Acetate in water with TEA to reduce emulsions. The organic layer was dried over Magnesium Sulfate, filtered and concentrated to give 4-amino-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide. 100 mg of 4-amino-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide was reacted with 30 μL of Methanesulfonyl Chloride and 90 μL DIPEA in 500 μL DCM. The reaction mixture was evaporated, subjected to basic workup conditions and purified by reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonylamide)benzamide. MS (Q1) 402 (M)+.

Workup

  1. concentrationUpon completion, the reaction was concentrated
  2. extractionextracted with Ethyl Acetate in water with TEA
  3. dry with materialThe organic layer was dried over Magnesium Sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2d74a847d2414ddbac7e21e55cc864b8
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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