Hydrogen Bromide → HCID 59344696, compound

HRID 18022Notes

Reaction equation

HRID 18022 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[F:38])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:32]C)[C:10](=[O:31])[N:11]3[CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[C:16](=[O:30])[C:12]3=2)[C:7]1=[O:34].Br>C(O)(=O)C.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[F:38])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:32])[C:10](=[O:31])[N:11]3[CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:22][CH2:23][N:24]4[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)[C:16](=[O:30])[C:12]3=2)[C:7]1=[O:34]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 6699789611-(3-Chloro-4-fluorobenzyl)-9-methoxy-2-(2-morpholin-4-ylethyl)-3,4,5,6,12,13-hexahydro-2h[1,4]diazocino[2,1-a]-2,6-naphthyridine-1,8,10(11h)-trione

Product 1

HCID 59344696HCID 59344696, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 11-(3-chloro-4-fluorobenzyl)-9-methoxy-2-(2-morpholin-4-ylethyl)-3,4,5,6,12,13-hexahydro-2H[1,4]diazocino[2,1-a]-2,6-naphthyridine-1,8,10(11H)-trione (30 mg, 0.06 mmol) and 33% hydrogen bromide in acetic acid (0.4 mL) in dioxane (2 mL) was stirred at room temperature for 30 minutes. 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 13.3 (s, 1H), 7.35 (dd, J=2.0, 7.0 Hz, 1H), 7.22-7.17 (m, 1H), 7.13 (t, J=8.7 Hz, 1H), 4.84-4.76 (m, 1H), 4.67 (app q, J=14.5 Hz, 2H), 4.43-4.36 (m, 1H), 4.02-2.85 (br signal, 17H), 2.66-2.60 (m, 1H), 2.11-2.01 (br m, 1H), 1.94 (br m, 1H), 1.78-1.69 (br m, 2H). (ES MS M+1=533.3)

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-25df17d65dd34db4afa75861efc3d9fd
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Reaction notes

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