Triethylamine → HCID 16772947, compound

HRID 1520366Notes

Reaction equation

HRID 1520366 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CCN(CC)CC.[N:21]1[CH:26]=[CH:25][N:24]=[CH:23][C:22]=1[C:27](Cl)=[O:28]>C1COCC1>[N+:11]([C:8]1[CH:9]=[CH:10][C:2]([NH:1][C:27]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][N:21]=2)=[O:28])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 120322-Amino-5-nitrobenzoic acidHCID 88279Pyrazinecarbonyl chloride

Product 1

HCID 16772947HCID 16772947, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of pyrazine-2-carboxylic acid (1.36 g, 10.9 mmol, 1 eq.) in SOCl2 (20 mL) was added DMF (2 drops). The mixture was stirred at 60° C. for 2.0 min. The volatiles were removed in vacuo to give crude pyrazine-2-carbonyl chloride, which was used in the next step directly. TO a suspension of 2-amino-5-nitrobenzoic acid (2.00 g, 10.9 mmol, 1.0 eq.) in THF (50 mL) was added Et3N (1.09 g) and pyrazine-2-carbonyl chloride in anhydrous THF (50 mL) dropwise. The resulting mixture was stirred at room temperature for 18 h. After the reaction was completed, the volatiles were removed. The residue was suspended in H2O (10 mL) and the pH was adjusted to 5 by slow addition of 2N HCl in water. The resulting solid was collected and dried in vacuo to give 3.12 g of 5-nitro-2-(pyrazine-2-carboxamido)benzoic acid as a brown solid (99%). LCMS m/z=289.0 (M+1) (Method B) (retention time=1.24 min),

Workup

  1. customthe volatiles were removed
  2. additionthe pH was adjusted to 5 by slow addition of 2N HCl in water
  3. customThe resulting solid was collected
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c5774395021b46f59add7bff674ddcf9
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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