Lithium Hydroxide → 3-(2H-1,2,3-triazol-2-yl)phenylamino-6-chloro-5-cyanonicotinic acid

HRID 2201089Notes

Reaction equation

HRID 2201089 reaction equation
[C:1]([C:3]1[C:4]([Cl:15])=[N:5][C:6](Cl)=[C:7]([CH:13]=1)[C:8]([O:10]CC)=[O:9])#[N:2].[N:16]1[N:17](C2C=C(C=CC=2)N)[N:18]=[CH:19][CH:20]=1.CC[N:30]([CH:34]([CH3:36])[CH3:35])C(C)C.[Li+].[OH-].[CH2:39]1[CH2:43]OC[CH2:40]1>C(#N)C.O>[N:16]1[N:17]([C:7]2([CH:13]=[C:3]([C:1]#[N:2])[C:4]([Cl:15])=[N:5][CH:6]2[NH:30][C:34]2[CH:35]=[CH:43][CH:39]=[CH:40][CH:36]=2)[C:8]([OH:10])=[O:9])[N:18]=[CH:19][CH:20]=1

Participants

8

Reactant 5

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 234387563-(2H-1,2,3-Triazol-2-yl)anilineHCID 71425174Ethyl 2,6-dichloro-5-cyanopyridine-3-carboxylate

Product 1

HCID 866661613-(2H-1,2,3-triazol-2-yl)phenylamino-6-chloro-5-cyanonicotinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a suspension of ethyl 5-cyano-2,6-dichloronicotinate Q4 (1.10 g, 4.4 mmol) in ACN (20 ml) was added 3-(2H-1,2,3-triazol-2-yl)aniline Q5 (774 mg, 4.84 mmol) and DIPEA (1.18 mL, 6.6 mmol). The mixture was stirred at ambient temperature for 15 h, and diluted with water; the resulting precipitate was collected by filtration to give intermediate, which was added THF (12 mL) and a solution of LiOH (106 mg, 8.8 mmol) in water (6 mL). After stirring at ambient temperature for 2 h, THF was removed by concentration and the residue was acidified to pH 2, the resulting precipitate was collected by filtration to give 2-(3-(2H-1,2,3-triazol-2-yl)phenylamino-6-chloro-5-cyanonicotinic acid Q6 (870 mg).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customto give intermediate, which
  3. stirringAfter stirring at ambient temperature for 2 h
  4. customTHF was removed by concentration
  5. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-7eec766a20ef4c3b86f106a02f75fa80
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

Loading…