1-Hydroxybenzotriazole → HCID 118113468, compound

HRID 713643Notes

Reaction equation

HRID 713643 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.[Cl:12][C:13]1[C:14]([C:19](O)=[O:20])=[N:15][CH:16]=[CH:17][CH:18]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[Cl:12][C:13]1[C:14]([C:19]([NH:1][C:2]2[CH:7]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:5]=[CH:4][N:3]=2)=[O:20])=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 8246323-Chloropyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27783152-Amino-4-(trifluoromethyl)pyridine

Product 1

HCID 118113468HCID 118113468, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 0.81 g of 2-amino-4-trifluoromethylpyridine, 0.78 g of 3-chloropicolinic acid, 1.15 g of EDCI hydrochloride, 0.06 g of HOBt and 10 mL of pyridine was stirred at 70° C. for 2 hours. A saturated aqueous sodium bicarbonate solution was poured to the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting solid was washed with hexane and dried to obtain 1.33 g of 3-chloro-N-(4-trifluoromethylpyridin-2-yl)picolinamide.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washthe resulting solid was washed with hexane
  5. customdried

Sources & evidence

ORD record
ord-b893da7c7d2343608c9f4d36aab689c4
Source dataset
uspto-grants-2015_11
Patent number
US09185910B2

Reaction notes

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