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

HRID 530908Notes

Reaction equation

HRID 530908 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-5fa5fde9cc70490bbc94a6f6946b5b98
Source dataset
uspto-grants-2016_05
Patent number
US09353110B2

Reaction notes

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