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Diisopropylethylamine → 3-(2-Chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethoxyphenyl)piperazine-1-carboxylate

HRID 856190
Notes
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Reaction equation

HRID 856190 reaction equation
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16](Cl)=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C(N(CC)C(C)C)(C)C.[Cl:30][C:31]1[N:32]([CH2:39][C:40]([OH:44])([CH3:43])[CH2:41][OH:42])[CH:33]=[C:34]([N+:36]([O-:38])=[O:37])[N:35]=1>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:42][CH2:41][C:40]([OH:44])([CH3:43])[CH2:39][N:32]3[CH:33]=[C:34]([N+:36]([O-:38])=[O:37])[N:35]=[C:31]3[Cl:30])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 23081081(2R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-methyl-1,2-propanediolHCID 230812344-(4-Trifluoromethoxyphenyl)piperazine-1-carbonylchloride

Product 1

HCID 694795383-(2-Chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethoxyphenyl)piperazine-1-carboxylateYield 55.6%

Reagents, catalysts & solvents 3

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

4-(4-Trifluoromethoxyphenyl)piperazine-1-carbonylchloride (0.26 g, 0.85 mmol), N,N-diisopropylethylamine (0.30 ml, 1.7 mmol) and 4-dimethylaminopyridine (21 mg, 0.17 mmol) were added to a suspension of 2-chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazol prepared in Example 3 (0.30 g, 1.3 mmol) in toluene (5 ml) followed by stirring at 100° C. for 2.5 hours. The mixture was diluted with ethyl acetate, washed with water, 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 3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethoxyphenyl)piperazine-1-carboxylate (0.24 g, yield 55%) as a light yellow oil.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-8f375fd7d9a74aeb8bc51c57aa3435be
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07262212B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes