Diisopropylethylamine → N-(3(2-((dimethylamino)methyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-iodo-4-methylbenzamide

HRID 923200Notes

Reaction equation

HRID 923200 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](Cl)=[O:6].[CH3:12][N:13]([CH2:15][C:16]1[N:17]([C:21]2[CH:22]=[C:23]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=2)[NH2:24])[CH:18]=[CH:19][N:20]=1)[CH3:14].CCN(C(C)C)C(C)C>C1COCC1>[CH3:14][N:13]([CH2:15][C:16]1[N:17]([C:21]2[CH:22]=[C:23]([NH:24][C:5](=[O:6])[C:4]3[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([I:1])[CH:3]=3)[CH:25]=[C:26]([C:28]([F:29])([F:31])[F:30])[CH:27]=2)[CH:18]=[CH:19][N:20]=1)[CH3:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 177521573-Iodo-4-methylbenzoyl chlorideHCID 468386103-(2-((Dimethylamino)methyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

Product 1

HCID 46838614N-(3(2-((dimethylamino)methyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-iodo-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Iodo-4-methylbenzoyl chloride (2.2 g, 7.88 mmol), dissolved in anhydrous THF (13 mL), was added dropwise to a solution of 3-(2-((dimethylamino)methyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (1.5 g, 5.5 mmol), DIPEA (2.1 mL, 11.8 mmol) in THF (30 mL) at ˜5° C. The resultant solution was stirred at ambient temperature overnight. The solvent was removed in vacuo and the crude residue was redissolved in CH2Cl2 and washed with 1N NaOH. The organic layer was then washed with water, and brine then dried over NaSO4 before being concentrated in vacuo. The brown colored residue was then triturated in a mixture of hexanes/DCM to precipitate 1.4 g of the desired product as an off-white powder: 529 m/z (M+H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe crude residue was redissolved in CH2Cl2
  3. washwashed with 1N NaOH
  4. washThe organic layer was then washed with water, and brine
  5. dry with materialthen dried over NaSO4
  6. concentrationbefore being concentrated in vacuo
  7. customThe brown colored residue was then triturated in a mixture of hexanes/DCM
  8. customto precipitate 1.4 g of the desired product as an off-white powder

Sources & evidence

ORD record
ord-ad2bd85b00d247c0940732a37185cccd
Source dataset
uspto-grants-2016_03
Patent number
US09278971B2

Reaction notes

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