Triethylamine → HCID 50896496, compound

HRID 631498Notes

Reaction equation

HRID 631498 reaction equation
[NH2:1]/[C:2](/OCC)=[CH:3]\[C:4](=O)[C:5]([F:8])([F:7])[F:6].Cl.[F:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][NH2:22])=[CH:17][CH:16]=1.C(N(CC)CC)C>>[F:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:2]([NH2:1])=[CH:3][C:4]([C:5]([F:6])([F:7])[F:8])=[N:22]2)=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 151117544-Amino-4-ethoxy-1,1,1-trifluorobut-3-en-2-one

Product 1

HCID 50896496HCID 50896496, compoundYield 64%

Procedure

According to the procedure described in Example 161A Step 3, using (E)-4-amino-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (2.747 g, 15 mmol), (4-fluorophenyl)hydrazine hydrochloride (2.439 g, 15 mmol), and triethylamine (2.03 g, 20 mmol) at 95° C. for 8 hours, which was purified by silica gel chromatography with 5-25% EtOAc/hexane as eluants to afford 1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-amine as solid (2.346 g, 64%). 1H NMR (300 MHz, CDCl3) 67.55 (m, 2H), 7.20 (m, 2H), 5.87 (s, 1H), 3.87 (br, 2H); LC-MS (ESI) m/z 246 (M+H)+.

Workup

  1. customat 95° C.
  2. customfor 8 hours
  3. customwhich was purified by silica gel chromatography with 5-25% EtOAc/hexane as eluants

Sources & evidence

ORD record
ord-fedbf18562744314bed37c1e08af0c00
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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