Diisopropylethylamine → HCID 69481807, compound

HRID 856197Notes

Reaction equation

[Cl:1][C:2]1[N:3]([CH2:10][C@:11]([OH:15])([CH3:14])[CH2:12][OH:13])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.C(N(CC)C(C)C)(C)C.[F:25][C:26]([F:45])([F:44])[C:27]1[CH:43]=[CH:42][C:30]([CH:31]=[N:32][N:33]2[CH2:38][CH2:37][N:36]([C:39](Cl)=[O:40])[CH2:35][CH2:34]2)=[CH:29][CH:28]=1>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:45][C:26]([F:25])([F:44])[C:27]1[CH:43]=[CH:42][C:30]([CH:31]=[N:32][N:33]2[CH2:34][CH2:35][N:36]([C:39]([O:13][CH2:12][C@@:11]([OH:15])([CH3:14])[CH2:10][N:3]3[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=[C:2]3[Cl:1])=[O:40])[CH2:37][CH2:38]2)=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

(R)-2-Chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazole prepared in Example 10 (2.75 g, 11.66 mmol), N,N-diisopropylethylamine (2.71 ml, 15.54 mmol) and 4-dimethylaminopyridine (0.19 g, 1.55 mmol) were added to a suspension of 4-(4-trifluoromethylbenzylideneamino)piperazine-1-carbonylchloride (2.48 g, 7.77 mmol) in toluene (40 ml) followed by stirring at 100° C. for 2.5 hours. The reaction mixture was diluted with ethyl acetate, washed with 10% hydrochloric acid, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1) to afford (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylbenzylideneamino)piperazine-1-carboxylate (4.03 g, quantitative) as a yellow oil.

Workup

washwashed with 10% hydrochloric acid
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1)

Sources & evidence

ORD record: ord-5caf75c797884aac8cba2f19c610ace8
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262212B2

Reaction notes

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