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M. Osorio-Olivares et al. / Bioorg. Med. Chem. 12 (2004) 4055–4066
(ArCOCH). HRMS m=z 275.0772, calculated for
C12H12F3NO3, 275.0769.
4.1.8. (R,S)-2-Trifluoroacetamido-1-(4-methylthiophen-
yl)-1-propanone (11). Yield 40%, mp 91–93 ꢁC. 1H
NMR (CDCl3) 1.52 (d, 3H, J ¼ 7:1 Hz, CH3CH), 2.55
(s, 3H, CH3S), 5.44–5.51 (m, 1H, CHCH3), 7.32 (d, 2H,
J ¼ 8:2 Hz, ArH-3,5), 7.65 (s, 1H, NH), 7.89 (d, 2H,
J ¼ 8:8 Hz, ArH-2,6). 13C NMR (CDCl3, 75 MHz) 14.6
(CH3CH), 19.5 (CH3S), 50.6 (CHCH3), 116.9 (q,
CF3CO), 125.1 (ArC-3,5), 128.8 (ArC-1), 129.2 (ArC-
2,6), 148.4 (ArC-4), 156.5 (q, CF3CO), 195.8 (Ar-
COCH). HRMS m=z 291.0542, calculated for
C12H12F3NO2S, 291.0541.
4.1.4. (R,S)-2-Trifluoroacetamido-1-(4-ethoxyphenyl)-1-
propanone (7). Yield 51%, mp 93–94 ꢁC. 1H NMR
(CDCl3) 1.46 (t, 3H, J ¼ 7:0 Hz, CH3CH2O), 1.52 (d,
3H, J ¼ 7:0 Hz, CH3CH), 4.13 (q, 2H, J ¼ 7:0 Hz,
CH3CH2O), 5.48 (m, 1H, CHCH3), 6.98 (d, 2H,
J ¼ 8:9 Hz, ArH-3,5), 7.68 (br s, 1H, NH), 7.96 (d, 2H,
J ¼ 8:9 Hz, ArH-2,6). 13C NMR (CDCl3) 14.6
(CH3CH), 19.6 (CH3CH2O), 50.6 (CHCH3), 64.0
(CH3CH2O), 115.8 (q, CF3CO), 114.7 (ArC-3,5), 125.5
(ArC-1), 131.2 (ArC-2,6), 156.5 (q, CF3CO), 164.1
(ArC-4), 195.3 (ArCOCH). HRMS m=z 289.0924, cal-
culated for C13H14F3NO3, 289.0926.
4.1.9. (R,S)-2-Trifluoroacetamido-1-(4-ethylthiophenyl)-
1
1-propanone (12). Yield 27%, mp 86–88 ꢁC. H NMR
(CDCl3) 1.40 (t, 3H, J ¼ 7:7 Hz, CH3CH2S), 1.52 (d,
3H, J ¼ 7:1 Hz, CH3CH), 3.05 (q, 2H, J ¼ 7:7 Hz,
CH3CH2S), 5.5 (quintet, 1H, J ¼ 7:1 Hz, CH3CH), 7.33
(d, 2H, J ¼ 8:8 Hz, ArH-3,5), 7.63 (s, 1H, NH), 7.87 (d,
2H, J ¼ 8:2 Hz, Ar-2,6). 13C NMR (CDCl3) 13.8
(CH3CH), 19.5 (CH3CH2S), 25.8 (CH3CH2S), 50.6
(CHCH3), 115.7 (q, CF3CO), 126.1 (ArC-3,5), 129.0
(ArC-1), 129.2 (ArC-2,6), 147.4 (ArC-4), 156.5 (q,
CF3CO), 195.8 (ArCOCH). HRMS m=z 305.0701, cal-
culated for C13H14F3NO2S, 305.0697.
4.1.5. (R,S)-2-Trifluoroacetamido-1-(4-propoxyphenyl)-
1-propanone (8). Yield 50%, mp 63–65 ꢁC. 1H NMR
(CDCl3) 1.06 (t, 3H, J ¼ 7:3 Hz, CH3CH2CH2O), 1.52
(d, 3H, J ¼ 7:3 Hz, CHCH3), 1.85 (m, 2H,
CH3CH2CH2O), 4.01 (t, 2H, J ¼ 6:7 Hz, CH3CH2-
CH2O), 5.47 (m, 1H, CHCH3), 6.98 (d, 2H, J ¼ 8:5 Hz,
ArH-3,5), 7.65 (s, 1H, NH), 7.95 (d, 2H, J ¼ 9:1 Hz,
ArH-2,6). 13C NMR (CDCl3) 10.4 (CH3CH2CH2O),
19.6 (CHCH3), 22.4 (CH3CH2CH2O), 50.4 (CHCH3),
70.0 (CH3CH2CH2O), 117.5 (q, COCF3), 114.8 (ArC-
3,5), 125.5 (ArC-1), 131.3 (ArC-2,6), 156.0 (q, COCF3),
164.3 (ArC-4), 195.3 (ArCOCH). HRMS m=z 303.1079,
calculated for C14H16F3NO3, 303.1082.
4.1.10. (R,S)-2-Trifluoroacetamido-1-(4-propylthiophen-
yl)-1-propanone (13). Yield 35%, mp 79–80 ꢁC. 1H
NMR (CDCl3) 1.06 (t, 3H, J ¼ 7:4 Hz, CH3CH2CH2S),
1.49 (d, 3H, J ¼ 7:0 Hz, CHCH3), 1.68–1.80 (m, 2H,
CH3CH2CH2S), 2.98 (t, 2H, J ¼ 7:4 Hz, CH3CH2-
CH2S), 5.40–5.49 (m, 1H, CHCH3), 7.32 (d, 2H,
J ¼ 8:9 Hz, ArH-3,5), 7.57 (s, 1H, NH), 7.84 (d, 2H,
J ¼ 8:9 Hz, ArH-2,6). 13C NMR (CDCl3) 13.5
(CHCH3), 19.5 (CH3CH2CH2S), 22.1 (CH3CH2CH2S),
33.7 (CH3CH2CH2S), 50.6 (CHCH3), 115.8 (q, COCF3),
126.3 (ArC-3,5), 129.1 (ArC-1), 129.2 (ArC-2,6), 147.7
(ArC-4), 156.5 (q, COCF3), 195.8 (ArCOCH). HRMS
m=z 319.0857, calculated for C14H16O2F3NS, 319.0854.
4.1.6. (R,S)-2-Trifluoroacetamido-1-(4-butoxyphenyl)-1-
propanone (9). Yield 39%, mp 51–52 ꢁC. 1H NMR
(CDCl3) 0.92 (t, 3H, J ¼ 7:4 Hz, CH3CH2CH2CH2O),
1.39–1.47 (m, 5H, CHCH3 and CH3CH2CH2CH2O),
1.70–1.77 (m, 2H, CH3CH2CH2CH2O), 3.98 (t, 2H,
J ¼ 6:6 Hz, CH3CH2CH2CH2O), 5.41 (m, 1H, CHCH3),
6.91 (d, 2H, J ¼ 8:9 Hz, ArH-3,5), 7.58 (s, 1H, NH),
7.88 (d, 2H, J ¼ 8:9 Hz, ArH-2,6). 13C NMR (CDCl3)
14.0 (CH3CH2CH2CH2O), 19.4 (CHCH3), 19.9 (CH3-
CH2CH2CH2O), 31.3 (CH3CH2CH2CH2O), 50.7
(CHCH3), 68.4 (CH3CH2CH2CH2O), 116.1 (q,
COCF3), 115.1 (ArC-3,5), 125.7 (ArC-1), 131.5 (ArC-
2,6), 156.8 (q, COCF3), 164.6 (ArC-4), 195.5 (Ar-
COCH). HRMS m=z 317.1222, calculated for
C15H18F3NO3, 317.1239.
4.1.11. (R,S)-2-Trifluoroacetamido-1-(4-butylthiophenyl)-
1
1-propanone (14). Yield 26%, mp 76–78 ꢁC. H NMR
(CDCl3) 0.94 (t, 3H, J ¼ 7:4 Hz, CH3CH2CH2CH2S),
1.42–1.54 (m, 5H, CHCH3 and CH3CH2CH2CH2S),
1.64–1.74 (m, 2H, CH3CH2CH2CH2S), 3.00 (t, 2H,
J ¼ 7:4 Hz, CH3CH2CH2CH2S), 5.40–5.49 (m, 1H,
CHCH3), 7.31 (d, 2H, J ¼ 8:7 Hz, ArH-3,5), 7.58 (s, 1H,
NH), 7.84 (d, 2H, J ¼ 8:9 Hz, ArH-2,6). 13C NMR
(CDCl3) 13.6 (CHCH3), 19.5 (CH3CH2CH2CH2S), 19.9
(CH3CH2CH2CH2S), 30.7 (CH3CH2CH2CH2S), 31.4
(CH3CH2CH2CH2S), 50.6 (CHCH3), 115.7 (q, COCF3),
126.2 (ArC-3,5), 129.1 (ArC-1), 129.2 (ArC-2,6), 147.7
(ArC-4), 155.4 (q, COCF3), 195.8 (ArCOCH). HRMS
m=z 333.1012, calculated for C15H18O2F3NS, 333.1010.
4.1.7. (R,S)-2-Trifluoroacetamido-1-(4-isobutoxyphenyl)-
1
1-propanone (10). Yield 53%, mp 75–77 ꢁC. H NMR
(CDCl3) 1.03 (d, 6H, J ¼ 6:6 Hz, (CH3)2CHCH2O), 1.49
(d, 3H, J ¼ 7:2 Hz, CHCH3), 2.06–2.14 (m, 1H,
(CH3)2CHCH2O), 3.79 (d, 2H, J ¼ 6:4 Hz, (CH3)2-
CHCH2O), 5.40–5.49 (m, 1H, CHCH3), 6.96 (d, 2H,
J ¼ 8:9 Hz, ArH-3,5), 7.62 (s, 1H, NH), 7.93 (d, 2H,
J ¼ 9:0 Hz, ArH-2,6). 13C NMR (CDCl3) 19.1 ((CH3)2-
CHCH2O), 19.7 (CHCH3), 28.2 ((CH3)2CHCH2O), 50.4
(CHCH3), 74.8 ((CH3)2CHCH2O), 115.8 (q, COCF3),
114.8 (ArC-3,5), 125.5 (ArC-1), 131.2 (ArC-2,6), 156.4
(q, COCF3), 164.5 (ArC-4), 195.3 (ArCOCH). HRMS
m=z 317.1237, calculated for C15H18F3NO3, 317.1239.
4.1.12. (R,S)-2-Trifluoroacetamido-1-(4-isobutylthiophen-
yl)-1-propanone (15). Yield 14%, mp 74–75 ꢁC. 1H NMR
(CDCl3) 1.05 (d, 6H, J ¼ 6:8 Hz, (CH3)2CHCH2S), 1.49
(d, 3H, J ¼ 7:2 Hz, CHCH3), 1.87–2.00 (m, 1H,
(CH3)2CHCH2S), 2.87 (d, 2H, J ¼ 7:0 Hz, (CH3)2CH-