Triethylamine → 5-chloro-N-((1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide

HRID 499815Notes

Reaction equation

HRID 499815 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[F:44][C:45]1[CH:46]=[C:47]([N:52]2[CH:56]=[C:55]([CH2:57][NH2:58])[N:54]=[CH:53]2)[CH:48]=[CH:49][C:50]=1[I:51]>CN(C=O)C.CCOC(C)=O.O>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:58][CH2:57][C:55]2[N:54]=[CH:53][N:52]([C:47]3[CH:48]=[CH:49][C:50]([I:51])=[C:45]([F:44])[CH:46]=3)[CH:56]=2)=[O:9])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66974227(1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methanamine

Product 1

HCID 669741585-chloro-N-((1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamideYield 21.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-2-thiophenecarboxylic acid 1-5 (165 mg, 1.01 mmol) and triethylamine (0.300 mL, 2.16 mmol) in DMF (5 mL), BOP (472 mg, 1.07 mmol) was added. After 5 min of stirring, a solution of (1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methanamine (268 mg, 0.845 mmol) in DMF (4 mL) was added. The mixture was stirred at room temperature overnight. H2O and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo. The residue was purified by HPLC to give 5-chloro-N-((1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (83 mg).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe organic phase was separated
  3. washwashed with 5% NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-e97df0d2de2a4ea7a76f87e8818bd16a
Source dataset
uspto-grants-2010_08
Patent number
US07767697B2

Reaction notes

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