Hydrogen Bromide → HCID 59344729, compound

HRID 18018Notes

Reaction equation

HRID 18018 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][N:8]1[CH2:36][CH2:35][CH2:34][CH2:33][N:11]2[C:12](=[O:32])[C:13]([O:30]C)=[C:14]3[C:19]([CH2:18][CH2:17][N:16]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([F:27])=[C:23]([Cl:28])[CH:22]=4)[C:15]3=[O:29])=[C:10]2[C:9]1=[O:37])(C)(C)C.Br>C(O)(=O)C.O1CCOCC1>[Cl:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[F:27])[CH2:20][N:16]1[CH2:17][CH2:18][C:19]2[C:14](=[C:13]([OH:30])[C:12](=[O:32])[N:11]3[CH2:33][CH2:34][CH2:35][CH2:36][N:8]([CH2:7][C:6]([OH:38])=[O:5])[C:9](=[O:37])[C:10]3=2)[C:15]1=[O:29]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 86644105HCID 86644105, compound

Product 1

HCID 59344729HCID 59344729, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl[11-(3-chloro-4-fluorobenzyl)-9-methoxy-1,8,10-trioxo-1,3,4,5,6,8,10,11,12,13-decahydro-2H-[1,4]diazocino[2,1-a]-2,6-naphthyridin-2-yl]acetate (50 mg, 0.09 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=6.6, 2.1 Hz, 1H), 7.18 (br signal, 1H), 7.11 (t, J=8.4 Hz, 1H), 4.78 (d, J=14.8 Hz, 1H), 4.52 (d, J=14.8 Hz, 1H), 4.41 (d, J=17.8 Hz, 1H), 4.07 (d, J=17.8 Hz, 1H), 3.67 (m, 1H), 3.51-3.36 (m), 3.23 (br d, 1H), 2.96 (m), 2.60 (m, 1H), 2.08 (m), 1.96 (m), 1.76 (m). (ES MS M+1=478.2)

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-9c4ccaf2c5654a9b80bc71d6ce4779fb
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Reaction notes

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