Triethylamine → N-((1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methyl)-5-chlorothiophene-2-carboxamide

HRID 643009Notes

Reaction equation

HRID 643009 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.[Br:44][C:45]1[CH:46]=[CH:47][C:48]([N:51]2[CH:55]=[C:54]([CH2:56][NH2:57])[N:53]=[CH:52]2)=[N:49][CH:50]=1>CN(C=O)C.CCOC(C)=O.O>[Br:44][C:45]1[CH:46]=[CH:47][C:48]([N:51]2[CH:55]=[C:54]([CH2:56][NH:57][C:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:9])[N:53]=[CH:52]2)=[N:49][CH:50]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 68502878(1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanamine

Product 1

HCID 68507465N-((1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methyl)-5-chlorothiophene-2-carboxamideYield 21.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-2-thiophenecarboxylic acid (195 mg, 1.20 mmol) and triethylamine (0.400 mL, 2.87 mmol) in DMF (5 mL), BOP (550 mg, 1.24 mmol) was added. After 5 min of stirring, a solution of (1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanamine (253 mg, 1.00 mmol) in DMF (5 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, and concentrated in vacuo. The residue was purified by HPLC to give N-((1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methyl)-5-chlorothiophene-2-carboxamide (85 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-028b648dce5443338baad7827c4126f5
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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