42
4 Experimental Data
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:2) yielded the product
(60.8 mg, 70%) as a pale yellow solid.
1
H NMR (400 MHz, CDCl3): δ = 8.29 (d, J = 1.6 Hz, 1H
28
), 7.97–7.89 (m,
3H
Ar
), 7.69–7.59 (m, 3H
Ar
), 7.28–7.15 (m, 3H
Ar
), 7.05–7.00 (m, 2H
Ar
), 4.66 (dd, J
= 9.0, 6.1 Hz, 1H
1
), 3.76–3.67 (m, 1H
6
), 3.42–3.33 (m, 1H
9
), 3.31–3.20 (m, 2H
6,9
),
3.01 (s, 3H
11
), 2.63–2.42 (m, 2H
13
), 2.17–2.05 (m, 1H
Alk
), 1.94–1.70 (m, 4H
Alk
),
1.54–1.44 (m, 1H
Alk
) ppm;
13
C NMR (175 MHz, CDCl3): δ = 167.6 (C
2
), 140.7
(C
Ar
), 136.1 (C
Ar
), 135.0 (C
Ar
), 132.3 (C
Ar
), 129.5 (CH
Ar
), 129.2 (CH
Ar
), 128.9
(CH
Ar
), 128.6 (2CH
Ar
), 128.6 (2CH
Ar
), 128.1 (CH
Ar
), 127.7 (CH
Ar
), 126.4 (CH
Ar
),
122.6 (CH
Ar
), 56.4 (CH
1
), 46.6 (CH2
6
), 46.1 (CH2
9
), 32.3 (CH2
Alk
), 30.7 (CH3
11
),
29.7 (CH2
Alk
), 26.3 (CH2
Alk
), 24.2 (CH2
Alk
) ppm; IR (neat):
= 3058, 3025,
2969, 2876, 1642, 1447, 1336, 1159, 933, 751, 702, 651 cm
-1
; HRMS (ESI): m/z
calculated for [M+H]
+
(C25H29N2O3S) 437.1893, found 437.1892.
2.1l N-Methyl-N-(1-oxo-4-phenyl-1-(pyrrolidin-1-yl)butan-2-yl)pyridine-2-sulfonamide
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:2) yielded the product
(57.0 mg, 74%) as a pale yellow liquid.
1
H NMR (400 MHz, CDCl3): δ = 8.66–8.63 (m, 1H
27
), 7.92–7.83 (m,
2H
25,26
), 7.49–7.43 (m, 1H
Ar
), 7.31–7.24 (m, 2H
Ar
), 7.21–7.12 (m, 3H
Ar
), 4.81 (dd,
J = 8.0, 6.8 Hz, 2H
1
), 3.88–3.79 (m, 1H
6
), 3.45–3.32 (m, 2H
9
), 3.30–3.22 (m, 1H
6
),
3.04 (s, 3H
11
), 2.67–2.52 (m, 2H
Alk
), 2.20–2.09 (m, 1H
Alk
), 1.98–1.77 (m, 5H
Alk
),
1.60 (bs, 1H
Alk
) ppm;
13
C NMR (100 MHz, CDCl3): δ = 168.2 (C
2
), 157.2 (C
Ar
),
150.1 (CH
Ar
), 141.0 (C
Ar
), 137.9 (CH
Ar
), 128.6 (CH
Ar
), 128.6 (CH
Ar
), 126.7
(CH
Ar
), 126.3 (CH
Ar
), 122.8 (CH
Ar
), 56.9 (CH
1
), 46.6 (CH2
6
), 46.1 (CH2
9
), 32.2
(CH2
Alk
), 30.9 (CH3
11
), 30.8 (CH2
Alk
), 26.3 (CH2
Alk
), 24.4 (CH2
Alk
). IR (neat):
= 3025, 2951, 2874, 1640, 1577, 1449, 1428, 1340, 1172, 1083, 937, 778,
744, 700, 589 cm
-1
; HRMS (ESI): m/z calculated for [M+Na]
+
(C20H25N3O3SNa) 410.1509, found 410.1507.
4 Experimental Data
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:2) yielded the product
(60.8 mg, 70%) as a pale yellow solid.
1
H NMR (400 MHz, CDCl3): δ = 8.29 (d, J = 1.6 Hz, 1H
28
), 7.97–7.89 (m,
3H
Ar
), 7.69–7.59 (m, 3H
Ar
), 7.28–7.15 (m, 3H
Ar
), 7.05–7.00 (m, 2H
Ar
), 4.66 (dd, J
= 9.0, 6.1 Hz, 1H
1
), 3.76–3.67 (m, 1H
6
), 3.42–3.33 (m, 1H
9
), 3.31–3.20 (m, 2H
6,9
),
3.01 (s, 3H
11
), 2.63–2.42 (m, 2H
13
), 2.17–2.05 (m, 1H
Alk
), 1.94–1.70 (m, 4H
Alk
),
1.54–1.44 (m, 1H
Alk
) ppm;
13
C NMR (175 MHz, CDCl3): δ = 167.6 (C
2
), 140.7
(C
Ar
), 136.1 (C
Ar
), 135.0 (C
Ar
), 132.3 (C
Ar
), 129.5 (CH
Ar
), 129.2 (CH
Ar
), 128.9
(CH
Ar
), 128.6 (2CH
Ar
), 128.6 (2CH
Ar
), 128.1 (CH
Ar
), 127.7 (CH
Ar
), 126.4 (CH
Ar
),
122.6 (CH
Ar
), 56.4 (CH
1
), 46.6 (CH2
6
), 46.1 (CH2
9
), 32.3 (CH2
Alk
), 30.7 (CH3
11
),
29.7 (CH2
Alk
), 26.3 (CH2
Alk
), 24.2 (CH2
Alk
) ppm; IR (neat):
= 3058, 3025,
2969, 2876, 1642, 1447, 1336, 1159, 933, 751, 702, 651 cm
-1
; HRMS (ESI): m/z
calculated for [M+H]
+
(C25H29N2O3S) 437.1893, found 437.1892.
2.1l N-Methyl-N-(1-oxo-4-phenyl-1-(pyrrolidin-1-yl)butan-2-yl)pyridine-2-sulfonamide
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:2) yielded the product
(57.0 mg, 74%) as a pale yellow liquid.
1
H NMR (400 MHz, CDCl3): δ = 8.66–8.63 (m, 1H
27
), 7.92–7.83 (m,
2H
25,26
), 7.49–7.43 (m, 1H
Ar
), 7.31–7.24 (m, 2H
Ar
), 7.21–7.12 (m, 3H
Ar
), 4.81 (dd,
J = 8.0, 6.8 Hz, 2H
1
), 3.88–3.79 (m, 1H
6
), 3.45–3.32 (m, 2H
9
), 3.30–3.22 (m, 1H
6
),
3.04 (s, 3H
11
), 2.67–2.52 (m, 2H
Alk
), 2.20–2.09 (m, 1H
Alk
), 1.98–1.77 (m, 5H
Alk
),
1.60 (bs, 1H
Alk
) ppm;
13
C NMR (100 MHz, CDCl3): δ = 168.2 (C
2
), 157.2 (C
Ar
),
150.1 (CH
Ar
), 141.0 (C
Ar
), 137.9 (CH
Ar
), 128.6 (CH
Ar
), 128.6 (CH
Ar
), 126.7
(CH
Ar
), 126.3 (CH
Ar
), 122.8 (CH
Ar
), 56.9 (CH
1
), 46.6 (CH2
6
), 46.1 (CH2
9
), 32.2
(CH2
Alk
), 30.9 (CH3
11
), 30.8 (CH2
Alk
), 26.3 (CH2
Alk
), 24.4 (CH2
Alk
). IR (neat):
= 3025, 2951, 2874, 1640, 1577, 1449, 1428, 1340, 1172, 1083, 937, 778,
744, 700, 589 cm
-1
; HRMS (ESI): m/z calculated for [M+Na]
+
(C20H25N3O3SNa) 410.1509, found 410.1507.