N-Iodosuccinamide → HCID 54683933, compound

HRID 1817358Notes

Reaction equation

HRID 1817358 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[F:30])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:25])[C:10](=[O:24])[N:11]([CH:21]([CH3:23])[CH3:22])[C:12]=2[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[C:7]1=[O:26].[I:31]NC(=O)CCC(N)=O>FC(F)(F)S(O)(=O)=O.CO>[Cl:1][C:2]1[C:29]([F:30])=[CH:28][C:27]([I:31])=[C:4]([CH:3]=1)[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:25])[C:10](=[O:24])[N:11]([CH:21]([CH3:23])[CH3:22])[C:12]=2[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[C:7]1=[O:26]

Participants

5

Reactant 2

HCID 21864724N-IodosuccinamideHCID 54680316HCID 54680316, compound

Product 1

HCID 54683933HCID 54683933, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

A mixture of 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-N,N-dimethyl-2-isopropyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide (43 mg, 0.10 mmol; Example 13) and N-iodosuccinamide (22 mg, 0.1 mmol) in trifluoromethanesulfonic acid at 0° C. was stirred for 10 minutes. The mixture was diluted with methanol and subjected to preparative HPLC purification on C-18 reverse stationary phase column eluting with a gradient of water—acetonitrile in the presence of 0.1% trifluoroacetic acid. Collection and lyophilization of appropriate fractions provided the titled compound.

Workup

  1. customsubjected to preparative HPLC purification on C-18 reverse stationary phase column
  2. washeluting with a gradient of water—acetonitrile in the presence of 0.1% trifluoroacetic acid
  3. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-33f534276b534401aaa3054208ad46bc
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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