Acetic Acid → HCID 59344730, compound

HRID 18026Notes

Reaction equation

HRID 18026 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:30])[C:10](=[O:29])[N:11]3[CH2:21][CH2:20][CH:19](N4CCCC4)[CH2:18][N:17]([CH3:27])[C:16](=[O:28])[C:12]3=2)[C:7]1=[O:31].Br.C(O)(=[O:39])C>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:30])[C:10](=[O:29])[N:11]3[CH2:21][CH2:20][C:19](=[O:39])[CH2:18][N:17]([CH3:27])[C:16](=[O:28])[C:12]3=2)[C:7]1=[O:31]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 59344763HCID 59344763, compound

Product 1

HCID 59344730HCID 59344730, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 11-(3-chloro-4-fluorobenzyl)-9-hydroxy-2-methyl-4-pyrrolidin-1-yl-3,4,5,6,12,13-hexahydro-2H[1,4]diazocino[2,1-a]-2,6-naphthyridine-1,8,10(11H)-trione (40 mg, 0.08 mmol) and 33% hydrogen bromide in acetic acid (0.5 mL) in dioxane (1 mL) was stirred at room temperature for 1.5 hour. 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-66a30d1282174ff7a35d68877891ae0e
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Reaction notes

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