1-Hydroxybenzotriazole → HCID 178477293, compound

HRID 2201376Notes

Reaction equation

HRID 2201376 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.[CH2:14]([S:16][C:17]1[C:22]([C:23](O)=[O:24])=[CH:21][N:20]=[CH:19][CH:18]=1)[CH3:15].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>O.N1C=CC=CC=1>[CH2:14]([S:16][C:17]1[C:22]([C:23]([NH:1][C:2]2[C:3]([SH:12])=[N:4][CH:5]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:7]=2)=[O:24])=[CH:21][N:20]=[CH:19][CH:18]=1)[CH3:15]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1179887074-Ethylsulfanylnicotinic acid hydrochlorideHCID 178507667HCID 178507667, compound

Product 1

HCID 178477293HCID 178477293, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 450 mg of 3-amino-5-trifluoromethylpyridine-2-thiol, 637 mg of 4-ethylsulfanylnicotinic acid hydrochloride, 532 mg of EDCI hydrochloride, 31 mg of HOBt and 5 ml of pyridine was stirred at room temperature for 2 hours and then stirred at 60° C. for 30 minutes. Water was poured to the reaction mixture, and the precipitated solid was filtered. The resulting solid was washed with water and n-hexane and then dried to obtain 494 mg of 4-ethylsulfanyl-N-[2-mercapto-5-(trifluoromethyl)pyridin-3-yl]nicotinamide. 4-ethylsulfanyl-N-[2-mercapto-5-(trifluoromethyl)pyridin-3-yl]nicotinamide

Workup

  1. stirringstirred at 60° C. for 30 minutes
  2. filtrationthe precipitated solid was filtered
  3. washThe resulting solid was washed with water and n-hexane
  4. customdried

Sources & evidence

ORD record
ord-40aafddc2db44988857d67f62799199e
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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