1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-Chloropyridin-2-carboxylic acid (2-mercapto-5-trifluoromethylpyridin-3-yl)-amide

HRID 1477294Notes

Reaction equation

HRID 1477294 reaction equation
[NH2:1][C:2]1[C:3]([SH:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[Cl:13][C:14]1[C:15]([C:20](O)=[O:21])=[N:16][CH:17]=[CH:18][CH:19]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>O.N1C=CC=CC=1>[SH:12][C:3]1[C:2]([NH:1][C:20]([C:15]2[C:14]([Cl:13])=[CH:19][CH:18]=[CH:17][N:16]=2)=[O:21])=[CH:7][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 8246323-Chloropyridine-2-carboxylic acidHCID 178507667HCID 178507667, compound

Product 1

HCID 1785221603-Chloropyridin-2-carboxylic acid (2-mercapto-5-trifluoromethylpyridin-3-yl)-amideYield 58.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 3-amino-5-trifluoromethylpyridin-2-thiol (0.45 g), 3-chloropyridin-2-carboxylic acid (0.39 g), WSC (0.67 g), HOBt (31 mg) and pyridine (4 ml) was stirred at room temperature for 12 hours. To the reaction mixture was added water, and the mixture was filtered to collect a solid. The resulting solid was washed with water, followed by n-hexane, and dried to give 3-chloropyridin-2-carboxylic acid (2-mercapto-5-trifluoromethylpyridin-3-yl)-amide (0.45 g), which is hereinafter referred to as “intermediate compound (M20-11)”.

Workup

  1. filtrationthe mixture was filtered
  2. customto collect a solid
  3. washThe resulting solid was washed with water
  4. customdried

Sources & evidence

ORD record
ord-8cd8835d71164b0188e1bbd557caea96
Source dataset
uspto-grants-2016_08
Patent number
US09403771B2

Reaction notes

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