Methyl morpholine oxide → 11-(3-Chloro-4-fluorobenzyl)-9-methoxy-2-methyl-5,6,12,13-tetrahydro-2h[1,4]diazocino[2,1-a]-2,6-naphthyridine-1,4,8,10(3h, 11h)-tetrone

HRID 2066602Notes

Reaction equation

HRID 2066602 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:26][CH3:27])[C:10](=[O:25])[N:11]3[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18][N:17]([CH3:23])[C:16](=[O:24])[C:12]3=2)[C:7]1=[O:28].C[N+]1([O-])CCOCC1>ClCCl.[Ru+3].C([N+](CCC)(CCC)CCC)CC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:26][CH3:27])[C:10](=[O:25])[N:11]3[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][N:17]([CH3:23])[C:16](=[O:24])[C:12]3=2)[C:7]1=[O:28]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 66997031HCID 66997031, compound

Product 1

HCID 6725311811-(3-Chloro-4-fluorobenzyl)-9-methoxy-2-methyl-5,6,12,13-tetrahydro-2h[1,4]diazocino[2,1-a]-2,6-naphthyridine-1,4,8,10(3h, 11h)-tetrone

Reagents, catalysts & solvents 2

HCID 131726442HCID 131726442, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 11-(3-chloro-4-fluorobenzyl)-4-hydroxy-9-methoxy-2-methyl-3,4,5,6,12,13-hexahydro-2H[1,4]diazocino[2,1-a]-2,6-naphthyridine-1,8,10(11H)-trione (50 mg, 0.11 mmol), molecular sieves (4A), N-methylmorpholine N-oxide (19 mg, 0.16 mmol), and tetra-n-propylammonium ruthenium tetroxide in dichloromethane was stirred at room temperature for two hrs. The mixture was filtered, and the filtrate concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 0-15% methanol in dichloromethane gradient. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated under vacuum
  3. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-d1480da0986a41f1b286eb85cb4e4d6f
Source dataset
uspto-grants-2012_10
Patent number
US08293731B2

Reaction notes

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