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 18023Notes

Reaction equation

HRID 18023 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-14ae93f0e2fc4239bc147c2f8b2320e3
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Reaction notes

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