Water → 5-Chloro-N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide

HRID 642998Notes

Reaction equation

HRID 642998 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[I:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([CH2:22][NH2:23])[N:19]=[CH:18]2)=[CH:13][CH:12]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:23][CH2:22][C:20]2[N:19]=[CH:18][N:17]([C:14]3[CH:15]=[CH:16][C:11]([I:10])=[CH:12][CH:13]=3)[CH:21]=2)=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 592601094-Aminomethyl 1-(4-iodophenyl)imidazole

Product 1

HCID 249868975-Chloro-N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamideYield 97.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-chlorothiophene-2-carboxylic acid (0.346 g, 2.13 mmol), (1-(4-iodophenyl)-1H-imidazol-4-yl)methanamine 9.7 (0.578 g, 1.93 mmol) and TEA (0.670 mL, 4.82 mmol) in DMF (10 mL), BOP (1.03 g, 2.33 mmol) was added. The mixture was then stirred at room temperature overnight. Water and EtOAc were added. The organic layer was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give the title compound as a solid (0.832 g). MS found for C15H11ClIN3OS: 443.9 and 445.9 ((M+H)+, Cl pattern).

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with 5% NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-457a9dffa60a47b6afb1fc43b9c37483
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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