Pyridine → HCID 67442688, compound

HRID 474214Notes

Reaction equation

HRID 474214 reaction equation
OC1C=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH:27]=[CH:28][CH:29]=2)[CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]3[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=3)[C:22]#[N:23])=[N:13]2)=[N:6]C=1.N1C=C[CH:33]=[CH:32][CH:31]=1.Cl[C:37]([O:39][CH:40]([CH3:42])[CH3:41])=[O:38]>ClCCl.C1(C)C=CC=CC=1>[CH:32]([C:37]([O:39][C:40]1[CH:42]=[N:6][C:5]([C:8]2[CH:29]=[CH:28][CH:27]=[C:10]([CH2:11][N:12]3[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]4[CH:26]=[CH:25][CH:24]=[C:21]([C:22]#[N:23])[CH:20]=4)=[N:13]3)[CH:9]=2)=[N:4][CH:41]=1)=[O:38])([CH3:33])[CH3:31]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 58477511HCID 58477511, compound

Product 1

HCID 67442688HCID 67442688, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

1.14 g (3 mmol) of 3-{1-[3-(5-hydroxypyrimidin-2-yl)benzyl]-6-oxo-1,6-dihydropyridazin-3-yl}benzonitrile are suspended in 15 ml of dichloromethane, 242 μl [3 mmol) of pyridine are added, and 3.0 ml of 1 M isopropyl chloroformate solution in toluene are added dropwise at 0-5° C. with stirring. The mixture is stirred at room temperature for 24 h. The reaction mixture is filtered, the mother liquor is washed with water, dried, filtered and stripped off to dryness. The residue is purified by column chromatography on silica gel. The product is triturated with ether, filtered off with suction and dried.

Workup

  1. stirringThe mixture is stirred at room temperature for 24 h
  2. filtrationThe reaction mixture is filtered
  3. washthe mother liquor is washed with water
  4. customdried
  5. filtrationfiltered
  6. customThe residue is purified by column chromatography on silica gel
  7. customThe product is triturated with ether
  8. filtrationfiltered off with suction
  9. customdried

Sources & evidence

ORD record
ord-984a5732e8c6498697f57d509faa159b
Source dataset
uspto-grants-2014_01
Patent number
US08637518B2

Reaction notes

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