2-Nitroimidazole → HCID 86724822, compound

HRID 1525586Notes

Reaction equation

HRID 1525586 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH2:22][C@@H:23]([CH3:37])[C@@H:24]([CH3:36])[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].C(=O)([O-])[O-].[K+].[K+].[N+:44]([C:47]1[NH:48][CH:49]=[CH:50][N:51]=1)([O-:46])=[O:45]>>[CH3:35][O:34][C:28]1[CH:27]=[C:26]([CH2:25][C@H:24]([CH3:36])[C@H:23]([CH3:37])[CH2:22][C:16]2[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:14]([O:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][N:48]3[CH:49]=[CH:50][N:51]=[C:47]3[N+:44]([O-:46])=[O:45])[CH:15]=2)[CH:31]=[CH:30][C:29]=1[O:32][CH3:33]

Participants

4

Reactant 3

HCID 107012-NitroimidazoleHCID 11430Potassium CarbonateHCID 86724821HCID 86724821, compound

Product 1

HCID 86724822HCID 86724822, compoundYield 85.1%

Procedure

The Standard Procedure 2 was followed by use of 5b (135.1 mg, 0.2315 mmol, 1.0 equiv), potassium carbonate (67.5 mg, 0.488 mmol, 2.1 equiv), and 2-nitroimidazole (6b, 54.3 mg, 0.485 mmol, 2.0 equiv). After workup and purification with column chromatography (80% EtOAc in hexanes as eluant), 7d (121.2 mg, 0.1970 mmol) was obtained in 85% yield as a yellow gummy oil: 1H NMR (CDCl3, 400 MHz) δ 0.81 (d, J=6.4 Hz, 6H, 2×CH3), 1.73 (m, 2H, 2×CH), 2.23-2.29 (m, 2H, 2×ArCH), 2.69-2.74 (m, 2H, 2×ArCH), 3.56-3.86 (m, 21H, 3×OCH3+6×OCH2), 4.12 (t, J=5.0 Hz, 2H, CH2N), 4.56 (t, J=4.8 Hz, 2H, CH2O), 6.62 (s, 1H, ArH), 6.67-6.69 (m, 3H, 3×ArH), 6.75-6.78 (m, 2H, 2×ArH), 7.08 (s, 1H, nitroimidazole C5-H), 7.23 (s, 1H, nitroimidazole C4-H); 13C NMR (CDCl3, 100 MHz) δ 16.05, 16.07, 38.63, 38.68, 39.09, 39.12, 49.71, 55.66, 55.76, 55.82, 68.30, 69.22, 69.58, 70.37, 70.46, 70.47, 70.61, 110.89, 111.56, 112.10, 114.58, 120.82, 121.56, 127.30, 127.86, 134.34, 134.40, 144.57, 146.88, 147.41, 147.77, 148.54; IR (neat) 2925 (s), 2873 (s), 1590 (w), 1538 (m), 1516 (s), 1456 (w), 1361 (s), 1260 (s), 1236 (s), 1029 (s) cm−1; HRMS (FAB) m/z calcd for C32H46N3O9 (M+H)+: 616.3234. found: 616.3231.

Workup

  1. customAfter workup and purification with column chromatography (80% EtOAc in hexanes as eluant)

Sources & evidence

ORD record
ord-c161e4c8d66f4d39979a9779bb383a43
Source dataset
uspto-grants-2015_07
Patent number
US09084779B2

Reaction notes

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