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Aniline → HCID 178521929, compound

HRID 659801
Notes
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Reaction equation

HRID 659801 reaction equation
[C:1]1([C:7]2[C:8]([C:12]([OH:14])=O)=[N:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:16]1([NH:15][C:12]([C:8]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:11][NH:10][N:9]=2)=[O:14])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178524945HCID 178524945, compound

Product 1

HCID 178521929HCID 178521929, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A solution of 4-phenyl-1H-pyrazole-3-carboxylic acid (75 mg; 0.4 mmol) (prepared according to Example 228C), aniline (45 μl; 0.48 mmol), EDAC (92 mg; 0.48 mmol) and HOBt (65 mg; 0.48 mmol) in 5 ml of DMF was stirred at room temperature overnight. The reaction was evaporated then purified by flash column chromatography eluting with 1:3 then 1:2 ethyl acetate/hexane. Product containing fractions were combined and evaporated to give 30 mg of 4-phenyl-1H-pyrazole-3-carboxylic acid phenylamide as a white solid. (LC/MS: Rt 3.12 [M+H]+ 264).

Workup

  1. customThe reaction was evaporated
  2. customthen purified by flash column chromatography
  3. washeluting with 1:3
  4. additionProduct containing fractions
  5. customevaporated

Sources & evidence

ORD record
ord-13e1be8acdae456d9c160933853f2735
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08080666B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes