4-Cyanobenzoic acid → HCID 178513318, compound

HRID 1364803Notes

Reaction equation

HRID 1364803 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 (M)+.

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-0fd38a1c23ef4561b837ce66916e575a
Source dataset
uspto-grants-2011_02
Patent number
US07888364B2

Reaction notes

Loading…