5-Chloro-2-thiophenecarboxylic acid → HCID 178523075, compound

HRID 2357782Notes

Reaction equation

HRID 2357782 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=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.[NH2:37][CH2:38][C:39]1[N:40]=[CH:41][NH:42][CH:43]=1>CN(C=O)C>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:37][CH2:38][C:39]2[N:40]=[CH:41][NH:42][CH:43]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 950485-Chloro-2-thiophenecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178510438HCID 178510438, compound

Product 1

HCID 178523075HCID 178523075, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chlorothiophene-2-carboxylic acid 1-5 (1.10 g, 6.76 mmol) and TEA (2.0 mL, 14.4 mmol) in DMF (12 mL), BOP (3.30 g, 7.45 mmol) was added. After being mixed for 5 min, the solution was added to the compound 4-aminomethylimidazole II-2 prepared above (0.604 g, 6.22 mmol) in a round bottom flask. The mixture was then stirred at room temperature overnight. It was purified by HPLC to give 5-chloro-N-((1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 3-1 (1.52 g). MS 242.0 and 244.0 (M+H, Cl pattern).

Workup

  1. additionAfter being mixed for 5 min
  2. customprepared above (0.604 g, 6.22 mmol) in a round bottom flask
  3. customIt was purified by HPLC

Sources & evidence

ORD record
ord-496a9da832144fbab2be8ab47b641b72
Source dataset
uspto-grants-2010_07
Patent number
US07763608B2

Reaction notes

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