Pyridine → HCID 72731612, compound

HRID 654248Notes

Reaction equation

HRID 654248 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:19][CH:18]=1)=O.Cl.[NH2:32][OH:33].N1C=CC=CC=1>C(O)C.C(OCC)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:19][CH:18]=1)=[N:32][OH:33]

Participants

6

Reactant 3

HCID 1049PyridineHCID 60870DarglitazoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 72731612HCID 72731612, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Title product of Example 9 (0.10 g, 0.238 mmol), hydroxylamine hydrochloride (0.041 g, 0.595 mmol) and 2 mL of pyridine were combined in 3 mL of ethanol and the mixture stirred 18 hours at room temperature, then stripped of solvent and the residue taken up in 7.5 mL ethyl acetate, washed with 5 mL of cold 18% HCl and then 5 mL brine, dried (MgSO4) and stripped to yield 0.086 g of present title product as a white solid; mp 202°-205° C.; tlc Rf 0.53 (1:1 hexane:ethyl acetate).

Workup

  1. washwashed with 5 mL of cold 18% HCl
  2. dry with material5 mL brine, dried (MgSO4)

Sources & evidence

ORD record
ord-1b7f3e78ccaf467dac16e44f5cdbadf0
Source dataset
uspto-grants-1992_07
Patent number
US05130379

Reaction notes

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