Triethylamine → HCID 66974125, compound

HRID 1802653Notes

Reaction equation

HRID 1802653 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.[I:44][C:45]1[CH:50]=[CH:49][C:48]([N:51]2[CH:55]=[C:54]([CH2:56][NH2:57])[N:53]=[C:52]2[S:58][CH3:59])=[CH:47][CH:46]=1>CN(C=O)C.CCOC(C)=O.O>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:57][CH2:56][C:54]2[N:53]=[C:52]([S:58][CH3:59])[N:51]([C:48]3[CH:47]=[CH:46][C:45]([I:44])=[CH:50][CH:49]=3)[CH:55]=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 66974219HCID 66974219, compound

Product 1

HCID 66974125HCID 66974125, compoundYield 30.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-thiophene-2-carboxylic acid 1-5 (72 mg, 0.44 mmol) and triethylamine (0.150 mL, 1.10 mmol) in DMF (5 mL), BOP (235 mg, 0.53 mmol) was added. After 5 min of stirring, the solution was added to the sample of (1-(4-iodophenyl)-2-(methylthio)-1H-imidazol-4-yl)methanamine (127 mg, 0.37 mmol) in a flask. After being 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 dissolved in CH3CN (8 mL), H2O (10 mL) was added to induce precipitation, which was collected and dried on vacuum to give 5-chloro-N-((1-(4-iodophenyl)-2-(methylthio)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (56 mg).

Workup

  1. stirringAfter being 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. dissolutionThe residue was dissolved in CH3CN (8 mL)
  7. additionH2O (10 mL) was added
  8. customprecipitation, which
  9. customwas collected
  10. customdried on vacuum

Sources & evidence

ORD record
ord-a5bd12c675224aa98d8d489c41a76da7
Source dataset
uspto-grants-2013_01
Patent number
US08349873B2

Reaction notes

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