2-Nitroimidazole → HCID 86724827, compound

HRID 1525590Notes

Reaction equation

HRID 1525590 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:19]=[CH:18][C:17]([CH2:20][C@@H:21]([CH3:35])[C@@H:22]([CH3:34])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=2)=[CH:16][C:15]=1[O:36][CH3:37].C(=O)([O-])[O-].[K+].[K+].[N+:44]([C:47]1[NH:48][CH:49]=[CH:50][N:51]=1)([O-:46])=[O:45]>>[CH3:33][O:32][C:26]1[CH:25]=[C:24]([CH2:23][C@H:22]([CH3:34])[C@H:21]([CH3:35])[CH2:20][C:17]2[CH:18]=[CH:19][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])=[C:15]([O:36][CH3:37])[CH:16]=2)[CH:29]=[CH:28][C:27]=1[O:30][CH3:31]

Participants

4

Reactant 3

HCID 107012-NitroimidazoleHCID 11430Potassium CarbonateHCID 86724826HCID 86724826, compound

Product 1

HCID 86724827HCID 86724827, compoundYield 83.3%

Procedure

The Standard Procedure 2 was followed by use of 9b (36.6 mg, 0.0627 mmol, 1.0 equiv), potassium carbonate (18.0 mg, 0.130 mmol, 2.1 equiv), and 2-nitroimidazole (6b, 14.4 mg, 0.126 mmol, 2.0 equiv). After workup and purification with column chromatography (80% EtOAc in hexanes as eluant), 10d (32.1 mg, 0.0522 mmol) was obtained in 83% yield as a yellow gummy oil: 1H NMR (CDCl3, 400 MHz) δ 0.81 (d, J=6.4 Hz, 3H, CH3), 0.82 (d, J=6.4 Hz, 3H, CH3), 1.73 (m, 2H, 2×CH), 2.25-2.31 (m, 2H, 2×ArCH), 2.73-2.75 (m, 2H, 2×ArCH), 3.57-3.86 (m, 21H, 3×OCH3+6×OCH2), 4.12 (t, J=5.0 Hz, 2H, CH2N), 4.56 (t, J=4.8 Hz, 2H, CH2O), 6.62-6.68 (m, 4H, 4×ArH), 6.75-6.79 (m, 2H, 2×ArH), 7.08 (s, 1H, nitroimidazole C5-H), 7.23 (s, 1H, nitroimidazole C4-H); 13C NMR (CDCl3, 100 MHz) δ 16.08, 16.14, 38.71, 38.80, 39.06, 39.16, 49.77, 55.73, 55.76, 55.83, 68.56, 69.28, 69.67, 70.43 70.54, 70.65, 110.96, 112.20, 112.77, 113.64, 120.85, 120.95, 127.31, 127.91, 134.37, 135.23, 144.62, 146.12, 146.96, 148.61, 149.23; IR (neat) 2925 (s), 2868 (s), 1655 (w), 1590 (w), 1515 (s), 1488 (w), 1459 (m), 1362 (s), 1260 (s), 1030 (s) cm−1; HRMS (FAB) m/z calcd for C32H46N3O9 (M+H)+: 616.3234. found: 616.3234.

Workup

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

Sources & evidence

ORD record
ord-a769ef8b4e9646bcbbf13f8654ddf148
Source dataset
uspto-grants-2015_07
Patent number
US09084779B2

Reaction notes

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