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Trichloroacetyl chloride → 1-(3-Methoxy-benzyl)-1H-imidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

HRID 900252
Notes
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Reaction equation

HRID 900252 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=1)[CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.CCN(CC)CC.ClC(Cl)(Cl)[C:24](Cl)=[O:25].[CH:29]([N:32]1[CH2:37][CH2:36][CH:35]([NH2:38])[CH2:34][CH2:33]1)([CH3:31])[CH3:30]>C(Cl)Cl>[CH:29]([N:32]1[CH2:37][CH2:36][CH:35]([NH:38][C:24]([C:8]2[N:7]([CH2:6][C:5]3[CH:12]=[CH:13][CH:14]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:11]=[CH:10][N:9]=2)=[O:25])[CH2:34][CH2:33]1)([CH3:31])[CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6420Trichloroacetyl chlorideHCID 8471Triethylamine2×HCID 31633331-(Propan-2-yl)piperidin-4-amineHCID 122293911-(3-methoxy-benzyl)-1H-imidazole

Product 1

HCID 104059941-(3-Methoxy-benzyl)-1H-imidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 1-(3-methoxy-benzyl)-1H-imidazole (100 mg) and NEt3 (147 μL) in DCM (5 mL) was added trichloroacetyl chloride (106 μL) dropwise. The mixture was stirred for 2 h at RT. More NEt3 (147 μL) and 1-isopropyl-piperidin-4-ylamine (76 mg) were added and stirring was continued for 1 h at RT. The mixture was quenched by the addition of MeOH, concentrated and the residue was purified by preparative HPLC. The fractions containing the product were evaporated to provide 30 mg of the title compound as its trifluoroacetate salt. MS (ESI+): m/e=357.

Workup

  1. stirringstirring
  2. waitwas continued for 1 h at RT
  3. customThe mixture was quenched by the addition of MeOH
  4. concentrationconcentrated
  5. customthe residue was purified by preparative HPLC
  6. additionThe fractions containing the product
  7. customwere evaporated

Sources & evidence

ORD record
ord-2176587afdc241b88c9ae1bfea7a4413
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07358268B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes