Acetic Acid → HCID 59344748, compound

HRID 18015Notes

Reaction equation

HRID 18015 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][C:39]=1[F:40])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:34]C)[C:10](=[O:33])[N:11]3[CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:22][CH2:23][O:24][CH2:25][C:26]4C=CC=CC=4)[C:16](=[O:32])[C:12]3=2)[C:7]1=[O:36].Br.C(O)(=[O:44])C>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][C:39]=1[F:40])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:34])[C:10](=[O:33])[N:11]3[CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:22][CH2:23][O:24][C:25](=[O:44])[CH3:26])[C:16](=[O:32])[C:12]3=2)[C:7]1=[O:36]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 66997775HCID 66997775, compound

Product 1

HCID 59344748HCID 59344748, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 11-(3-chloro-4-fluorobenzyl)-9-methoxy-2-[2-(benzyl-oxy)ethyl]-3,4,5,6,12,13-hexahydro-2H[1,4]diazocino[2,1-a]-2,6-naphthyridine-1,8,10(11H)-trione (120 mg, 0.21 mmol) and 33% hydrogen bromide in acetic acid (1 mL) in dioxane (1 mL) was stirred at room temperature for 1 hour. The product mixture was concentrated under vacuum. The residue was 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. 1H NMR (400 MHz, CDCl3) δ 7.34 (dd, J=6.7, 1.6 Hz, 1H), 7.18 (br signal, 1H), 7.12 (t, J=8.6 Hz, 1H), 4.79 (br signal), 4.76 (d, J=14.7 Hz, 1H), 4.54 (d, J=14.7 Hz, 1H), 4.46 (br signal), 4.18 (m, 2H), 3.48-3.25 (m), 3.00-2.93 (m), 2.61-2.57 (m), 2.03 (s, 3H), 2.09-1.75 (m). (ES MS M+1=506.2)

Workup

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

Sources & evidence

ORD record
ord-74f1839f17494550bb5bad9634e7810a
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Reaction notes

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