1,2-Dichloroethane → HCID 178522447, compound

HRID 2170558Notes

Reaction equation

HRID 2170558 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[C:25]([NH2:26])=[CH:24][NH:23][N:22]=2)=[O:20])=[CH:14][CH:13]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CS(C)=O>[F:11][C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19]([C:21]2[C:25]([NH:26][C:4](=[O:6])[C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=3[F:1])=[CH:24][NH:23][N:22]=2)=[O:20])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 99352-Fluorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 178508056HCID 178508056, compound

Product 1

HCID 178522447HCID 178522447, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Fluorobenzoic acid (36 mg, 0.25 mmol) was added to a solution of 4-amino-1H-pyrazole-3-carboxylic acid (4-fluoro-phenyl)-amide (50 mg, 0.23 mmol), EDC (53 mg, 0.27 mmol) and HOBt (37 mg, 0.27 mmol) in DMSO (1 ml). The reaction mixture was stirred at room temperature for 24 hours and purified by preparative LC/MS. Evaporation of product-containing fractions yielded the product as a white solid (15 mg, 19%). (LC/MS: Rt 3.91, [M+H]+ 342.66).

Workup

  1. custompurified by preparative LC/MS
  2. customEvaporation of product-containing fractions

Sources & evidence

ORD record
ord-204e3aa78b7f4046aa4e440764750569
Source dataset
uspto-grants-2015_06
Patent number
US09051278B2

Reaction notes

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