4-Cyanobenzoic acid → HCID 178513318, compound

HRID 633177Notes

Reaction equation

HRID 633177 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[C:15]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=1)#[N:16].ClC1C=CC(NC(=O)C2C=CC(C#N)=CC=2)=CC=1C1C=CC=CN=1.CCN(C(C)C)C(C)C.Cl.[NH2:60][OH:61]>CCO>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:21](=[O:23])[C:20]2[CH:24]=[CH:25][C:17]([C:15](=[NH:16])[NH:60][OH:61])=[CH:18][CH:19]=2)=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

7

Reactant 5

HCID 120874-Cyanobenzoic acidHCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 401519254-Chloro-3-(pyridin-2-yl)anilineHCID 66877347N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-cyanobenzamide

Product 1

HCID 178513318HCID 178513318, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

240 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 207 mg of 4-cyanobenzoic acid via Procedure G. To 445 mg of N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-cyanobenzamide and 2.5 mL of DIPEA in 10 mL of EtOH was added 793 mg Hydroxylamine Hydrochloride and heated to 60° C. until reaction was complete. The solvent was subsequently evaporated, extracted twice with water in Ethyl Acetate, dried with Magnesium Sulfate, filtered and concentrated. The crude product was purified by reverse phase HPLC to give pure N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(N-hydroxycarbamimidoyl)benzamide. MS (Q1) 367.4 (N)+.

Workup

  1. customThe solvent was subsequently evaporated
  2. extractionextracted twice with water in Ethyl Acetate
  3. dry with materialdried with Magnesium Sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-c360e13f388f495c9c25c322278104cf
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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