Pyridine → HCID 178527118, compound

HRID 851885Notes

Reaction equation

HRID 851885 reaction equation
[O:1]=[S:2]1(=[O:26])[C:7]2[CH:8]=[C:9]([O:12][C:13]3[CH:14]=[C:15]([C:19](=[N:21][OH:22])[NH2:20])[CH:16]=[CH:17][CH:18]=3)[CH:10]=[CH:11][C:6]=2[N:5]2[CH2:23][CH2:24][CH2:25][C:4]2=[N:3]1.N1C=CC=CC=1.[S:33](Cl)(Cl)=[O:34]>C1COCC1.C(Cl)Cl>[O:34]=[S:33]1[NH:20][C:19]([C:15]2[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=2)[O:12][C:9]2[CH:10]=[CH:11][C:6]3[N:5]4[CH2:23][CH2:24][CH2:25][C:4]4=[N:3][S:2](=[O:1])(=[O:26])[C:7]=3[CH:8]=2)=[N:21][O:22]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 86595484HCID 86595484, compound

Product 1

HCID 178527118HCID 178527118, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension, cooled to 0° C., of the product obtained in Step A of Example 13 (250 mg, 0.67 mmol) in 15 ml of THF there are added 109 μl (1.34 mmol) of pyridine and then, dropwise, 72 μl (1.01 mmol) of thionyl chloride dissolved in 3 ml of CH2Cl2. Stirring is carried out at 0° C. for 30 minutes and the mixture is allowed to come back to ambient temperature whilst stirring for a further hour. Evaporation to dryness is carried out and the residue is made more solid by triturating it in water. The precipitate is filtered off to yield the title product.

Workup

  1. customto come back to ambient temperature
  2. stirringwhilst stirring for a further hour
  3. customEvaporation to dryness
  4. customby triturating it in water
  5. filtrationThe precipitate is filtered off

Sources & evidence

ORD record
ord-eebac961e4f74e858504295b123e6236
Source dataset
uspto-grants-2007_08
Patent number
US07253163B2

Reaction notes

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