Diisopropylethylamine → HCID 44241803, compound

HRID 1446085Notes

Reaction equation

HRID 1446085 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:20]2[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]2=[O:30])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:12][CH:13]=1.Br[C:32]1[N:33]([CH2:40][C:41]2([CH3:44])[CH2:43][O:42]2)[CH:34]=[C:35]([N+:37]([O-:39])=[O:38])[N:36]=1.C(N(C(C)C)CC)(C)C>C(OC(O)C)C>[F:1][C:2]1[CH:3]=[C:4]([N:20]2[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]2=[O:30])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([CH2:43][C:41]3([CH3:44])[O:42][C:32]4=[N:36][C:35]([N+:37]([O-:39])=[O:38])=[CH:34][N:33]4[CH2:40]3)[CH2:16][CH2:15]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10136449HCID 10136449, compoundHCID 85107489HCID 85107489, compound

Product 1

HCID 44241803HCID 44241803, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 101298981-EthoxyethanolSolvent

Procedure

A solution of N-[((5S)-3-{3-fluoro-4-[6-(1-piperazinyl)-3-pyridinyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide (0.147 g, 0.355 mmol), 2-bromo-1-[(2-methyl-2-oxiranyl)methyl]-4-nitro-1H-imidazole (0.092 g, 0.35 mmol) and diisopropylethylamine (70 μL, 0.40 mmol) in ethoxyethanol (10 mL) was refluxed for 2.5 h. The solution was evaporated onto silica gel, column chromatography (0-10% MeOH/EtOAc, gradient elution) gave a solid which was reprecipitated from refluxing MeOH to give the titled compound (25 mg, 12%) as a cream solid. APCI MS m/z 595 (M+H). 1H NMR (400 MHz, DMSO-d6) δ 8.28 (bs, 1H), 8.21 (t, J=5.8 Hz, 1H), 8.12 (s, 1H), 7.70 (bdt, J=9.0, 2.2 Hz, 1H), 7.51-7.59 (m, 2H), 7.37 (dd, J=8.6, 2.2 Hz, 1H), 6.88 (d, J=9.0 Hz, 1H), 4.71-4.79 (m, 1H), 4.29 (d, J=10.7 Hz, 1H), 4.15 (t, J=9.0 Hz, 1H), 4.09 (d, J=10.7 Hz, 1H), 3.77 (dd, J=9.2, 6.5 Hz, 1H), 3.31-3.47 (m, 6H), 2.82 (d, J=14.7 Hz, 1H), 2.78 (d, J=14.7 Hz, 1H), 2.72-2.79 (m, 4H), 1.84 (s, 3H), 1.58 (s, 3H).

Workup

  1. customThe solution was evaporated onto silica gel, column chromatography (0-10% MeOH/EtOAc, gradient elution)
  2. customgave a solid which
  3. customwas reprecipitated
  4. temperaturefrom refluxing MeOH

Sources & evidence

ORD record
ord-bde0871fa5ed430e8fbfee51ab0daaa0
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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