Trifluoroacetic acid → 6-(2-(3-(3,4-dichlorophenylamino)-1,2,4-oxadiazol-5-yl)ethyl)-3,4-dihydroquinolin-2(1H)-one

HRID 1023173Notes

Reaction equation

HRID 1023173 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([CH2:15][CH2:16][C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[N:23](CC3C=CC(OC)=CC=3)[C:22](=[O:36])[CH2:21][CH2:20]4)[O:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([CH2:15][CH2:16][C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[NH:23][C:22](=[O:36])[CH2:21][CH2:20]4)[O:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 866804156-(2-(3-((3,4-dichlorophenyl)amino)-1,2,4-oxadiazol-5-yl)ethyl)-1-(4-methoxybenzyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 715421306-(2-(3-(3,4-dichlorophenylamino)-1,2,4-oxadiazol-5-yl)ethyl)-3,4-dihydroquinolin-2(1H)-oneYield 432.8%

Conditions

Temperature
60 °C

Procedure

To 6-(2-(3-(3,4-dichlorophenylamino)-1,2,4-oxadiazol-5-yl)ethyl)-1-(4-methoxybenzyl)-3,4-dihydroquinolin-2(1H)-one (0.06 g 0.011 mmol) was added TFA (0.13 g, 0.11 mmol) and anisole (0.012 mmol). The resulting reaction mixture was heated to 60° C. for 4 h. TFA and anisole were removed under vacuum and the crude material was washed with hexane and diethyl ether to afford 6-(2-(3-(3,4-dichlorophenylamino)-1,2,4-oxadiazol-5-yl)ethyl)-3,4-dihydroquinolin-2(1H)-one as a brown solid (19.2 mg, 41%). 1HNMR: 400 MHz, DMSO-d6: δ 2.45 (q, J=7.20 Hz, 2H), 2.84 (t, J=7.60 Hz, 2H), 2.99 (t, J=7.60 Hz, 2H), 3.17 (t, J=7.60 Hz, 2H), 6.77 (d, J=7.60 Hz, 1H), 7.03 (t, J=1.20 Hz, 1H), 7.10 (s, 1H), 7.40 (dd, J=2.40, 8.80 Hz, 1H), 7.57 (d, J=8.80 Hz, 1H), 7.70 (d, J=2.40 Hz, 1H), 10.00 (s, 1H), 10.23 (s, 1H). LCMS: RT 2.023 min; LCMS (ES-API), m/z 401.0 [M−H]−.

Workup

  1. customThe resulting reaction mixture
  2. customTFA and anisole were removed under vacuum
  3. washthe crude material was washed with hexane and diethyl ether

Sources & evidence

ORD record
ord-2f540a863ab34d5c91ac1870118ac156
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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