Triethylamine → 2-[(1-Benzothien-2-ylcarbonyl)amino]nicotinic acid

HRID 1992310Notes

Reaction equation

HRID 1992310 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(N(CC)CC)C.[S:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH:20]=[C:19]1[C:27](Cl)=[O:28]>CC(C)=O.O>[S:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH:20]=[C:19]1[C:27]([NH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 729302-Aminonicotinic acidHCID 142384Benzo[b]thiophene-2-carbonyl Chloride

Product 1

HCID 591303622-[(1-Benzothien-2-ylcarbonyl)amino]nicotinic acid

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a solution of 2-aminonicotinic acid (91.1 g, 8.0 mmol), triethylamine (2.7 mL, 19.1 mmol) and acetone/H2O (3:1, 100 mL) was added 1-benzothiophene-2-carbonyl chloride (2.04 g, 10.4 mmol) at 0° C. The resulting solution was allowed to warm to rt and stir overnight. The volatile solvent was removed under reduced pressure and the aqueous solution was acidified with HCl (conc.). The resulting precipitate was filtered and then washed with EtOAc and dried under reduced pressure to afford the product. (1.2 g, 52%). NMR (DMSO): 11.7(1H, broad), 8.60(1H, m); 8.36(1H, s); 8.25(1H, d); 8.07(1H, d); 8.02(1H, d); 7.51(2H, m); 7.36(1H, m).

Workup

  1. customThe volatile solvent was removed under reduced pressure
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with EtOAc
  4. customdried under reduced pressure
  5. customto afford the product

Sources & evidence

ORD record
ord-e153afc826ff4deab85d343498de10f4
Source dataset
uspto-grants-2010_01
Patent number
US07648986B2

Reaction notes

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