Hydrochloric Acid → HCID 131732725, compound

HRID 1470539Notes

Reaction equation

HRID 1470539 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:15]([C:16](=[O:18])[CH3:17])=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1.[F:19]C1C=CC(CC2N=CC=CC=2C=O)=CC=1.CO[C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:44]2[C:49]([CH:50]=CC(C3C=C(OC)C(OC)=C(OC)C=3)=O)=[CH:48][CH:47]=[CH:46][N:45]=2)=[CH:39][CH:38]=1.Cl>CO>[F:19][C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:44]2[C:49]([CH:50]=[CH:17][C:16]([C:15]3[C:10]([NH:9][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)=[N:11][CH:12]=[CH:13][CH:14]=3)=[O:18])=[CH:48][CH:47]=[CH:46][N:45]=2)=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 96611687HCID 96611687, compoundHCID 117992430HCID 117992430, compoundHCID 131732719HCID 131732719, compound

Product 1

HCID 131732725HCID 131732725, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(2-(4-methoxyphenylamino)pyridin-3-yl)ethanone (100 mg, 0.462 mmol) in methanol (5 mL) was added 2N Ba(OH)2solution (2 ml) and stirred for 5 minutes. Then added 2-(4-fluorobenzyl)nicotinaldehyde (112.03 mg, 0.462 mmol) and the reaction mixture was stirred at a temperature of 30° C. for 6h and the reaction was monitored by TLC. After 8h the reaction mixture is acidified with 2N HCl. The resulting precipitate was filtered, washed thoroughly with water and dried over anhydrous CaCl2. The precipitate was recrystallized using ethanol to obtain pure (8l) (164 mg, 90% yield).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed thoroughly with water
  3. dry with materialdried over anhydrous CaCl2
  4. customThe precipitate was recrystallized

Sources & evidence

ORD record
ord-3b74307b641c4f90a4b87f651e169757
Source dataset
uspto-grants-2015_04
Patent number
US09006451B1

Reaction notes

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