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Triethylamine → HCID 11952490, compound

HRID 2101492
Notes
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Reaction equation

HRID 2101492 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1.C(N(CC)CC)C.[CH3:32][O:33][C:34](=[O:37])[CH2:35]Br>C1COCC1.CCOC(C)=O>[CH3:32][O:33][C:34](=[O:37])[CH2:35][N:12]([CH2:11][C:7]1[N:6]([CH2:5][C:4]2[CH:21]=[C:22]([Cl:24])[CH:23]=[C:2]([Cl:1])[CH:3]=2)[CH:10]=[CH:9][N:8]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 11951591HCID 11951591, compound

Product 1

HCID 11952490HCID 11952490, compoundYield 30.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857
Ethyl Acetate
Solvent

Procedure

To a solution of [1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-amine (200 mg, 0.55 mmol) and triethylamine (0.18 mL, 1.37 mmol) in THF (2 mL) was added methylbromoacetate (78 uL, 0.82 mmol). The reaction was stirred at ambient temperature for 18 h before diluting with EtOAc (50 mL). The solution was washed with water (20 mL) and brine then dried over Na2SO4. The solvent was removed in vacuo and the residue purified by column chromatography (silica gel, 5% MeOH in CH2Cl2). The purified product was treated with excess 2N HCl in Et2O solution to afford the hydrochloride salt of the desired product 7e (74 mg, 26%): ESI MS m/z 436 [C21H20Cl2FN3O+H]+.

Workup

  1. washThe solution was washed with water (20 mL) and brine
  2. dry with materialthen dried over Na2SO4
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by column chromatography (silica gel, 5% MeOH in CH2Cl2)
  5. additionThe purified product was treated with excess 2N HCl in Et2O solution

Sources & evidence

ORD record
ord-6194b431ee904509956b18c983169be9
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07572921B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes