Acetic Acid → HCID 59344754, compound

HRID 18034Notes

Reaction equation

HRID 18034 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]([O:24]C)[C:10](=[O:23])[N:11]3[CH2:19][CH:18]([CH2:20][OH:21])[O:17][C:16](=[O:22])[C:12]3=2)[C:7]1=[O:26].Br.[C:32](O)(=[O:34])[CH3:33]>>[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:24])[C:10](=[O:23])[N:11]3[CH2:19][CH:18]([CH2:20][O:21][C:32](=[O:34])[CH3:33])[O:17][C:16](=[O:22])[C:12]3=2)[C:7]1=[O:26]

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 260Hydrogen BromideHCID 66997674HCID 66997674, compound

Product 1

HCID 59344754HCID 59344754, compound

Procedure

A mixture of 9-(3-chloro-4-fluorobenzyl)-3-(hydroxymethyl)-7-methoxy-3,4,10,11-tetrahydro[1,4]oxazino[3,4-a]-2,6-naphthyridine-1,6,8(9H)-trione (50 mg, 0.11 mmol) and 33% hydrogen bromide in acetic acid (0.1 g) in acetic acid (1 μL) was stirred at room temperature for 30 minutes. The product mixture was concentrated under vacuum. The residue was dissolved in DMSO and subjected to reverse phase column chromatography on C-18 stationary phase eluted with a 95-5% water-acetonitrile gradient. Collection and lyophilization of appropriate fractions afforded the title compound.

Workup

  1. concentrationThe product mixture was concentrated under vacuum
  2. dissolutionThe residue was dissolved in DMSO
  3. washeluted with a 95-5% water-acetonitrile gradient
  4. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-d069fb20a668400eae91af68a1c9b6f0
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Reaction notes

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