Dimethyl Sulfoxide → HCID 20816861, compound

HRID 897304Notes

Reaction equation

HRID 897304 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19]([OH:20])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12]([CH:21]3[S:27][CH2:26][CH2:25][NH:24][C:23](=[O:28])[CH2:22]3)[N:11]=2)=[O:9])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:39])C=1.ClCCl.CS(C)=O>CN(C=O)C.C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19]([OH:20])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12]([CH:21]3[S:27](=[O:39])[CH2:26][CH2:25][NH:24][C:23](=[O:28])[CH2:22]3)[N:11]=2)=[O:9])=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 22346432HCID 22346432, compound

Product 1

HCID 20816861HCID 20816861, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a cold (0° C.) solution of N-(4-fluorobenzyl)-8-hydroxy-5-(5-oxo-1,4-thiazepan-7-yl)[1,6]naphthyridine-7-carboxamide (Example 141) (0.22 g, 0.52 mmol) in DMF (25 mL), a solution of 3-chloroperbenzoic acid in dichloromethane (0.57 mmol, 0.129 g/mL) was added and stirred at room temperature for 2 hours. The product mixture was treated with DMSO (1 mL), diethyl ether (200 mL), and cooled in an ice bath. The resultant precipitate was filtered, dissolved in DMSO, and subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided the title compound.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationThe resultant precipitate was filtered
  3. dissolutiondissolved in DMSO
  4. customsubjected to HPLC purification on C-18 stationary phase
  5. washeluted with water/acetonitrile/TFA mobile phase
  6. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-d8d0b6d79e004d2eb7ef2f43100c6226
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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