Pyridine → HCID 136336335, compound

HRID 2218261Notes

Reaction equation

HRID 2218261 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[OH:14])[CH:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=2)[C:3]=1[CH2:22][OH:23].N1C=CC=CC=1.[Cl:30][CH2:31][CH2:32][C:33](Cl)=[O:34]>C1COCC1.O>[NH2:1][C:2]1[C:3]([CH2:22][OH:23])=[C:4]([C:15]2[CH:16]=[C:17]([NH:21][C:33](=[O:34])[CH2:32][CH2:31][Cl:30])[CH:18]=[CH:19][CH:20]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[OH:14])[N:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 693643-Chloropropionyl chlorideHCID 136336334HCID 136336334, compound

Product 1

HCID 136336335HCID 136336335, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) solution of 2-[6-amino-4-(3-aminophenyl)-5-(hydroxymethyl)-2-pyridinyl]phenol (0.100 g, 0.325 mmol) in THF (3 mL) including pyridine (0.028 mL, 0.34 mmol) was added 3-chloropropionyl chloride (0.043 g, 0.34 mmol). After being stirred for 30 minutes, the mixture was allowed to warm to room temperature and the stirring was continued for 2 hrs. The resulting mixture was diluted with water and extracted with ethyl acetate. The separated organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was crystallized with ethyl ether. The resulting solid was collected by filtration, washed with ethyl ether, and dried under reduced pressure to give N-{3-[2-amino-3-(hydroxymethyl)-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-3-chloropropanamide as a pale yellow solid (0.072 g, yield 56%).

Workup

  1. waitthe stirring was continued for 2 hrs
  2. extractionextracted with ethyl acetate
  3. washThe separated organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized with ethyl ether
  8. filtrationThe resulting solid was collected by filtration
  9. washwashed with ethyl ether
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-dadd8c086cc54affa17c17c50b40f532
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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