Diisopropylethylamine → HCID 58866193, compound

HRID 1354268Notes

Reaction equation

HRID 1354268 reaction equation
[F:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:12].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]([C:25]([F:28])([F:27])[F:26])=[C:23]([C:29](Cl)=[O:30])[CH:22]=[N:21]2)=[CH:16][CH:15]=1.CCN(C(C)C)C(C)C>C(#N)C>[F:1][C:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:12][C:29]([C:23]1[CH:22]=[N:21][N:20]([C:17]2[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=2)[C:24]=1[C:25]([F:28])([F:26])[F:27])=[O:30]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1455693-Amino-2-fluorobenzotrifluorideHCID 27366451-(4-Chlorophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carbonyl chloride

Product 1

HCID 58866193HCID 58866193, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Fluoro-3-trifluoromethyl-phenylamine (0.007 g; 0.039 mmol) was added to a suspension of 1-(4-chloro-phenyl)-5-trifluoromethyl-1H-pyrazole-4-carbonyl chloride (0.010 g; 0.032 mmol) and PS-DIEA (0.1 g) in acetonitrile (2 mL). The reaction mixture was shaken at room temperature for 12 h at which time PS-TSCl (0.2 g) high loading was added to remove the excess amine. After an additional 12 h of shaking, the reaction mixture was filtered and concentrated to give 1-(4-chloro-phenyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (2-fluoro-3-trifluoromethyl-phenyl)-amide. LCMS m/z=449.9 (M−H)−.

Workup

  1. additionwas added
  2. customto remove the excess amine
  3. stirringAfter an additional 12 h of shaking
  4. filtrationthe reaction mixture was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c79fed8b8f324a31b5572955ea36ccc1
Source dataset
uspto-grants-2007_05
Patent number
US07223782B2

Reaction notes

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