Trifluoroacetic acid → HCID 59490674, compound

HRID 2383402Notes

Reaction equation

[CH:1]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:13][O:14][C:15]1[CH:27]=[CH:26][C:18]([CH2:19][N:20]2[C:24]([NH2:25])=[CH:23][CH:22]=[N:21]2)=[CH:17][CH:16]=1.F[C:29](F)(F)C(O)=O>>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][N:20]2[C:24]3=[N:25][CH:29]=[C:10]4[CH2:9][CH2:8][CH2:7][C:6]5[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=5[C:11]4=[C:23]3[CH:22]=[N:21]2)=[CH:26][CH:27]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 70003Benzosuberone

HCID 31612621-((4-methoxyphenyl)methyl)-1H-pyrazol-5-amine

Product 1

HCID 59490674HCID 59490674, compoundYield 30%

Conditions

Temperature: 100 °C

Procedure

To a mixture of 6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (8.5 g, 39.5 mmol) and 1-(4-methoxybenzyl)-1H-pyrazol-5-amine (8.2 g, 44.47 mmol) was added trifluoroacetic acid (4.25 mL, 54.3 mmol). The reaction mixture was heated at 100° C. for 24 hours. On completion of the reaction, the solvent was removed under reduced pressure and the crude product was purified by flash column chromatography (SiO2, gradient from 5% EtOAc in hexanes to 30% EtOAc in hexanes) to give the desired product (4.2 g, 30%) as an off-colored solid. 1H NMR (CDCl3, 400 MHz) δ: 7.97 (s, 1H), 7.85 (s, 1H), 7.79 (d, J=7.2 Hz, 1H), 7.46-7.44 (m, 1H), 7.38 (d, J=7.6 Hz, 2H), 7.28 (s, 1H), 7.26 (s, 1H), 6.84 (d, J=7.6 Hz, 2H), 5.69 (s, 2H), 3.76 (s, 3H), 2.59 (q, J=6.0 Hz, 4H), 2.21 (quintet, J=7.2 Hz, 2H); LCMS [M+H]: 356.

Workup

customOn completion of the reaction
customthe solvent was removed under reduced pressure
customthe crude product was purified by flash column chromatography (SiO2, gradient from 5% EtOAc in hexanes to 30% EtOAc in hexanes)

Sources & evidence

ORD record: ord-9c152553fa22438dae00eb553f1f3764
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263610B2

Reaction notes

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