Triethylamine → HCID 50896499, compound

HRID 631501Notes

Reaction equation

[NH2:1]/[C:2](/OCC)=[CH:3]\[C:4](=O)[C:5]([F:8])([F:7])[F:6].Cl.[C:14]1([CH3:22])[CH:19]=[CH:18][C:17]([NH:20][NH2:21])=[CH:16][CH:15]=1.C(N(CC)CC)C>>[C:14]1([CH3:22])[CH:19]=[CH:18][C:17]([N:20]2[C:2]([NH2:1])=[CH:3][C:4]([C:5]([F:6])([F:7])[F:8])=[N:21]2)=[CH:16][CH:15]=1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 125044-Methylphenylhydrazine monohydrochloride

HCID 151117544-Amino-4-ethoxy-1,1,1-trifluorobut-3-en-2-one

Product 1

HCID 50896499HCID 50896499, compoundYield 62%

Conditions

Temperature: 95 °C

Procedure

According to the procedure described in Example 161A Step 3, (E)-4-amino-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (2.747 g, 15 mmol), p-tolylhydrazine hydrochloride (2.379 g, 15 mmol) and triethylamine (2.03 g, 20 mmol) were heated at 95° C. for 8 hours. The crude product was purified by silica gel chromatography with 5-25% EtOAc/hexane as eluants to afford 1-p-tolyl-3-(trifluoromethyl)-1H-pyrazol-5-amine as solid (2.237 g, 62%). 1H NMR (300 MHz, CDCl3) δ 7.42 (d, 2H), 7.30 (d, 2H), 5.84 (s, 1H), 3.88 (br, 2H), 2.41 (s, 3H); LC-MS (ESI) m/z 242 (M+H)+.

Workup

customThe crude product was purified by silica gel chromatography with 5-25% EtOAc/hexane as eluants

Sources & evidence

ORD record: ord-c33dc2f72fda4dacb816afb13305f18a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09320739B2

Reaction notes

Loading…