Acetic Acid → HCID 59344730, compound

HRID 2426481Notes

Reaction equation

HRID 2426481 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-45dad4ae24404c06bf4b3d6eddf18823
Source dataset
uspto-grants-2011_06
Patent number
US07968564B2

Reaction notes

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