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stringclasses
11 values
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stringlengths
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38
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17 values
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stringlengths
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float64
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244
10.1021_jacs.5b12081
Cc1cc(=O)oc2cc(Br)ccc12
15
15
[0.12085494 0.4390625 0.22428686 0.4890625 ]
[0.24198644 0.4390625 0.88276654 0.4734375 ]
13C NMR
101 MHz
CD2Cl2
160.2 (C1), 154.4 (C10), 152.5 (C3), 128.0 (C7), 126.4 (C6), 125.8 (C8), 120.6 (C9), 119.7 (C5), 115.8 (C2), 19.0 (C4)
null
[(160.2, None, None), (154.4, None, None), (152.5, None, None), (128.0, None, None), (126.4, None, None), (125.8, None, None), (120.6, None, None), (119.7, None, None), (115.8, None, None), (19.0, None, None)]
10
10
10
10.1021_jacs.5b12081
C(c1ccc2c(C)cc(=O)oc2c1)(F)(F)F
15
15
[0.11974872 0.72578125 0.2328601 0.78046875]
[0.24862379 0.72578125 0.88166032 0.76015625]
1H NMR
600 MHz
CD2Cl2
7.76 (ddq, J = 8.3, 1.0, 0.5 Hz, 1H; H6), 7.59 (dp, J = 1.9, 0.6 Hz, 1H; H9), 7.56 (ddq, J = 8.2, 1.8, 0.7 Hz, 1H; H7), 6.38 (q, J = 1.4 Hz, 1H; H2), 2.47 (d, J = 1.4 Hz, 3H; H4)
null
[('ddq', ['8.3Hz', '1.0Hz', '0.5Hz'], '1H', 7.76, 7.76), ('dp', ['1.9Hz', '0.6Hz'], '1H', 7.59, 7.59), ('ddq', ['8.2Hz', '1.8Hz', '0.7Hz'], '1H', 7.56, 7.56), ('q', ['1.4Hz'], '1H', 6.38, 6.38), ('d', ['1.4Hz'], '3H', 2.47, 2.47)]
7
5
7
10.1021_jacs.5b12081
C(c1ccc2c(C)cc(=O)oc2c1)(F)(F)F
15
15
[0.11974872 0.72578125 0.2328601 0.78046875]
[0.24862379 0.72578125 0.88166032 0.76015625]
19F NMR
564 MHz
CD2Cl2
-63.27
null
[(-63.27, None, None)]
3
1
1
10.1021_jacs.5b12081
O(c1cc2c(C)cc(=O)oc2c(OC)c1OC)C
16
16
[0.124865 0.20078125 0.24323094 0.26171875]
[0.26079225 0.20078125 0.8805541 0.23515625]
1H NMR
400 MHz
CD2Cl2
6.78 (s, 1H; H6), 6.18 (q, J = 1.0 Hz, 1H; H2), 3.98 (s, 3H; H13), 3.95 (s, 3H; H11), 3.89 (s, 3H; H12), 2.40 (d, J = 1.2 Hz, 3H; H4)
null
[('s', [], '1H', 6.78, 6.78), ('q', ['1.0Hz'], '1H', 6.18, 6.18), ('s', [], '3H', 3.98, 3.98), ('s', [], '3H', 3.95, 3.95), ('s', [], '3H', 3.89, 3.89), ('d', ['1.2Hz'], '3H', 2.4, 2.4)]
14
6
14
10.1021_jacs.5b12081
O(c1cc2c(C)cc(=O)oc2c(OC)c1OC)C
16
16
[0.124865 0.20078125 0.24323094 0.26171875]
[0.26079225 0.20078125 0.8805541 0.23515625]
13C NMR
101 MHz
CD2Cl2
160.9 (C1), 153.0 (C3), 150.5 (C8), 146.4 (C7), 143.2 (C10), 141.7 (C9), 116.1 (C5), 114.3 (C2), 101.7 (C6), 62.3 (C13), 61.8 (C11), 56.9 (C12), 19.3 (C4)
null
[(160.9, None, None), (153.0, None, None), (150.5, None, None), (146.4, None, None), (143.2, None, None), (141.7, None, None), (116.1, None, None), (114.3, None, None), (101.7, None, None), (62.3, None, None), (61.8, None, None), (56.9, None, None), (19.3, None, None)]
13
13
13
10.1021_jacs.5b12081
Cc1cc(=O)oc2c1ccc1ccccc12
16
16
[0.12251428 0.48828125 0.22539309 0.55390625]
[0.24281611 0.48828125 0.88221343 0.52265625]
1H NMR
400 MHz
CD2Cl2
8.55-8.49 (m, 1H; H12), 7.96-7.87 (m, 1H; H9), 7.74 (dd, J = 8.9, 0.8 Hz, 1H; H6), 7.66 (t, J = 3.0 Hz, 2H; H1011), 7.65 (t, J = 2.6 Hz, 1H; H7), 6.35 (q, J = 1.3 Hz, 1H; H2), 2.53 (d, J = 1.3 Hz, 3H; H4)
null
[('m', [], '1H', 8.55, 8.49), ('m', [], '1H', 7.96, 7.87), ('dd', ['8.9Hz', '0.8Hz'], '1H', 7.74, 7.74), ('t', ['3.0Hz'], '2H', 7.66, 7.66), ('t', ['2.6Hz'], '1H', 7.65, 7.65), ('q', ['1.3Hz'], '1H', 6.35, 6.35), ('d', ['1.3Hz'], '3H', 2.53, 2.53)]
10
8
10
10.1021_jacs.5b12081
Cc1cc(=O)oc2c1ccc1ccccc12
16
16
[0.12251428 0.48828125 0.22539309 0.55390625]
[0.24281611 0.48828125 0.88221343 0.52265625]
13C NMR
101 MHz
CD2Cl2
161.0 (C1), 154.1 (C3), 151.2 (C14), 135.4 (C13), 129.1 (C1012), 128.3 (C9), 127.6 (C1012), 124.5 (C6), 123.7 (C8), 122.9 (C13), 121.2 (C7), 115.9 (C5), 114.9 (C2), 19.6 (C4)
null
[(161.0, None, None), (154.1, None, None), (151.2, None, None), (135.4, None, None), (129.1, None, None), (128.3, None, None), (127.6, None, None), (124.5, None, None), (123.7, None, None), (122.9, None, None), (121.2, None, None), (115.9, None, None), (114.9, None, None), (19.6, None, None)]
14
14
14
10.1039_d1sc01483h
CC1(C)OB(c2ccc(/C=C/I)cc2)OC1(C)C
1
1
[0.12040566 0.57617191 0.31288899 0.65195318]
[0.33001091 0.56796877 0.89807149 0.66093753]
1H NMR
300 MHz
CDCl3
7.76 (d, J = 8.1 Hz, 2H), 7.44 (d, J = 14.9 Hz, 1H), 7.29 (d, J = 7.8 Hz, 2H), 6.92 (d, J = 14.9 Hz, 1H), 1.34 (s, 12H)
null
[('d', ['8.1Hz'], '2H', 7.76, 7.76), ('d', ['14.9Hz'], '1H', 7.44, 7.44), ('d', ['7.8Hz'], '2H', 7.29, 7.29), ('d', ['14.9Hz'], '1H', 6.92, 6.92), ('s', [], '12H', 1.34, 1.34)]
18
5
18
10.1039_d1sc01483h
Cc1cc(C)c(/C=C/I)c(C)c1
1
2
[0.09879615 0.82500003 0.22921258 0.87968753]
[0.09720824 0.07973633 0.89807149 0.17304688]
1H NMR
300 MHz
CDCl3
7.43 (d, J = 15.1 Hz, 1H), 6.86 (s, 2H), 6.28 (d, J = 15.1 Hz, 1H), 2.25 (s, 9H)
null
[('d', ['15.1Hz'], '1H', 7.43, 7.43), ('s', [], '2H', 6.86, 6.86), ('d', ['15.1Hz'], '1H', 6.28, 6.28), ('s', [], '9H', 2.25, 2.25)]
13
5
13
10.1039_d1sc01483h
Cc1cc(C)c(/C=C/I)c(C)c1
1
2
[0.09879615 0.82500003 0.22921258 0.87968753]
[0.09720824 0.07973633 0.89807149 0.17304688]
13C NMR
75 MHz
CDCl3
143.6, 137.3, 135.7, 134.9, 128.9, 80.0, 21.1, 20.9
null
[(143.6, None, None), (137.3, None, None), (135.7, None, None), (134.9, None, None), (128.9, None, None), (80.0, None, None), (21.1, None, None), (20.9, None, None)]
11
8
8
10.1021_jacs.8b09739
C(F)(F)(F)c1cc(NC(=S)NCc2ccccn2)cc(C(F)(F)F)c1
4
4
[0.55563342 0.60351566 0.69923648 0.65351567]
[0.14802163 0.68203126 0.84946742 0.88203129]
13C NMR
125 MHz
DMSO-d6
180.89, 156.99, 148.91, 142.02, 136.94, 130.49 (q, J=33.8Hz), 124.44 (q, J=271.2Hz), 122.52, 121.97, 121.73, 120.10, 116.24, 48.91
null
[(180.89, None, None), (156.99, None, None), (148.91, None, None), (142.02, None, None), (136.94, None, None), (130.49, 'q', 33.8), (124.44, 'q', 271.2), (122.52, None, None), (121.97, None, None), (121.73, None, None), (120.1, None, None), (116.24, None, None), (48.91, None, None)]
15
12
13
10.1021_jacs.8b09739
C(F)(F)(F)c1cc(NC(=S)NCc2cccnc2)cc(C(F)(F)F)c1
5
5
[0.55563342 0.29101564 0.69923648 0.34179691]
[0.1474693 0.35820315 0.85057205 0.5933594 ]
13C NMR
125 MHz
DMSO-d6
181.18, 148.95, 148.25, 141.83, 135.27, 134.05, 130.28 (q, J=32.80Hz), 124.14 (q, J=271.80Hz), 123.40, 122.33, 116.32, 44.73
null
[(181.18, None, None), (148.95, None, None), (148.25, None, None), (141.83, None, None), (135.27, None, None), (134.05, None, None), (130.28, 'q', 32.8), (124.14, 'q', 271.8), (123.4, None, None), (122.33, None, None), (116.32, None, None), (44.73, None, None)]
15
12
12
10.1021_jacs.8b09739
C(F)(F)(F)c1cc(NC(=S)Nc2ccccn2)cc(C(F)(F)F)c1
5
5
[0.56226124 0.66875003 0.69260866 0.71406254]
[0.14802163 0.74687503 0.84946742 0.90937504]
13C NMR
125 MHz
DMSO-d6
178.87, 153.26, 145.75, 140.87, 139.58, 130.38 (q, J=32.5Hz), 124.29 (q, J=271.2Hz), 124.68, 118.64, 118.30, 113.08
null
[(178.87, None, None), (153.26, None, None), (145.75, None, None), (140.87, None, None), (139.58, None, None), (130.38, 'q', 32.5), (124.29, 'q', 271.2), (124.68, None, None), (118.64, None, None), (118.3, None, None), (113.08, None, None)]
14
11
11
10.1021_jacs.8b09739
C(F)(F)(F)c1cc(NC(=S)Nc2cccnc2)cc(C(F)(F)F)c1
6
6
[0.56170895 0.26093751 0.69426563 0.31328128]
[0.14857395 0.34003907 0.84891508 0.57578127]
13C NMR
125 MHz
DMSO-d6
180.40, 145.84, 145.64, 142.05, 135.97, 131.75, 130.37 (q, J=32.9Hz), 125.11 (q, J=270.7Hz), 123.66, 123.51, 116.99
null
[(180.4, None, None), (145.84, None, None), (145.64, None, None), (142.05, None, None), (135.97, None, None), (131.75, None, None), (130.37, 'q', 32.9), (125.11, 'q', 270.7), (123.66, None, None), (123.51, None, None), (116.99, None, None)]
14
11
11
10.1021_jacs.8b09739
FC(F)(F)c1cc(NC(=S)NCc2cccc(Cl)n2)cc(C(F)(F)F)c1
16
16
[0.54569166 0.40781252 0.68487621 0.47031252]
[0.14912627 0.48828129 0.84836274 0.72421881]
13C NMR
125 MHz
DMSO-d6
181.15, 158.83, 149.59, 141.80, 140.25, 130.33 (q, J=33.2Hz), 125.94 (q, J=273.3Hz), 122.62, 122.16, 120.69, 116.31, 48.31
null
[(181.15, None, None), (158.83, None, None), (149.59, None, None), (141.8, None, None), (140.25, None, None), (130.33, 'q', 33.2), (125.94, 'q', 273.3), (122.62, None, None), (122.16, None, None), (120.69, None, None), (116.31, None, None), (48.31, None, None)]
15
12
12
10.1021_jacs.8b09739
CC(C)(C)c1ccc(CNC(=O)Nc2cc(C(F)(F)F)cc(C(F)(F)F)c2)c(Cl)n1
17
17
[0.53740686 0.66718754 0.70531202 0.72656257]
[0.14802163 0.76562507 0.84946742 0.89062507]
13C NMR
125 MHz
DMSO-d6
168.04, 154.88, 147.67, 142.38, 138.32, 130.77 (q, J=32.5Hz), 130.48, 124.43 (q, J=273.4Hz), 118.49, 117.38, 113.72, 40.23, 36.94, 29.73
null
[(168.04, None, None), (154.88, None, None), (147.67, None, None), (142.38, None, None), (138.32, None, None), (130.77, 'q', 32.5), (130.48, None, None), (124.43, 'q', 273.4), (118.49, None, None), (117.38, None, None), (113.72, None, None), (40.23, None, None), (36.94, None, None), (29.73, None, None)]
19
14
14
10.1021_jacs.8b09739
C(F)(F)(F)c1cc(NC(=S)NC2CCCCC2)cc(C(F)(F)F)c1
19
19
[0.56226124 0.66132817 0.69260866 0.70898445]
[0.14802163 0.72890626 0.84891508 0.89140628]
1H NMR
500 MHz
CDCl3
8.34 (bs, 1H), 7.70-7.75 (m, 3H), 6.07 (bs, 1H), 4.20 (m, 1H), 2.00-2.14 (m, 2H), 1.57-1.78 (m, 3H), 1.35-1.50 (m, 2H), 1.10-1.30 (m, 3H)
null
[('brs', [], '1H', 8.34, 8.34), ('m', [], '3H', 7.75, 7.7), ('brs', [], '1H', 6.07, 6.07), ('m', [], '1H', 4.2, 4.2), ('m', [], '2H', 2.14, 2.0), ('m', [], '3H', 1.78, 1.57), ('m', [], '2H', 1.5, 1.35), ('m', [], '3H', 1.3, 1.1)]
16
8
16
10.1021_jacs.8b09739
C(F)(F)(F)c1cc(NC(=S)NC2CCCCC2)cc(C(F)(F)F)c1
19
19
[0.56226124 0.66132817 0.69260866 0.70898445]
[0.14802163 0.72890626 0.84891508 0.89140628]
13C NMR
125 MHz
DMSO-d6
179.21, 142.04, 129.99 (q, J=33.0Hz), 124.17 (q, J=271.8Hz), 121.68, 115.74, 52.28, 31.58, 25.09, 24.42
null
[(179.21, None, None), (142.04, None, None), (129.99, 'q', 33.0), (124.17, 'q', 271.8), (121.68, None, None), (115.74, None, None), (52.28, None, None), (31.58, None, None), (25.09, None, None), (24.42, None, None)]
15
10
10
10.1021_jacs.8b09739
C(F)(F)(F)c1cc(NC(=S)Nc2cc(C(F)(F)F)cc(C(F)(F)F)c2)cc(C(F)(F)F)c1
20
20
[0.54790096 0.21640625 0.70475968 0.26640626]
[0.14691699 0.30234377 0.84836274 0.61250004]
1H NMR
500 MHz
DMSO-d6
10.66 (s, 2H), 8.20 (s, 4H), 7.88 (s, 2H)
null
[('s', [], '2H', 10.66, 10.66), ('s', [], '4H', 8.2, 8.2), ('s', [], '2H', 7.88, 7.88)]
8
3
8
10.1021_jacs.8b09739
C(F)(F)(F)c1cc(NC(=S)Nc2cc(C(F)(F)F)cc(C(F)(F)F)c2)cc(C(F)(F)F)c1
20
20
[0.54790096 0.21640625 0.70475968 0.26640626]
[0.14691699 0.30234377 0.84836274 0.61250004]
13C NMR
125 MHz
DMSO-d6
180.60, 141.19, 130.48 (q, J= 33.0Hz), 125.86 (q, J= 271.8Hz), 124.05, 117.62
null
[(180.6, None, None), (141.19, None, None), (130.48, 'q', 33.0), (125.86, 'q', 271.8), (124.05, None, None), (117.62, None, None)]
17
6
6
10.1021_acs.orglett.4c02707
C(F)(F)(F)c1ccc2c(Nc3c(C)cccc3C)nn(C)c2n1
1
1
[0.60863974 0.14316407 0.79264712 0.25429689]
[0.11449909 0.31640627 0.88465084 0.51250003]
1H NMR
400 MHz
CDCl3
7.22-7.11 (m, 3H), 7.10-6.99 (m, 2H), 5.85 (s, 1H), 4.00 (s, 3H), 2.24 (s, 6H)
null
[('m', [], '3H', 7.22, 7.11), ('m', [], '2H', 7.1, 6.99), ('s', [], '1H', 5.85, 5.85), ('s', [], '3H', 4.0, 4.0), ('s', [], '6H', 2.24, 2.24)]
15
7
15
10.1021_acs.orglett.4c02707
C(F)(F)(F)c1ccc2c(Nc3c(C)cccc3C)nn(C)c2n1
1
1
[0.60863974 0.14316407 0.79264712 0.25429689]
[0.11449909 0.31640627 0.88465084 0.51250003]
19F NMR
377 MHz
CDCl3
-67.11
null
[(-67.11, None, None)]
3
1
1
10.1021_acs.orglett.4c02707
C(F)(F)(F)c1ccc2c(Nc3ccc4c(c3)OCCO4)nn(C)c2n1
3
3
[0.11904872 0.45937502 0.32984837 0.57656252]
[0.11475184 0.59726565 0.8841453 0.69335945]
1H NMR
400 MHz
CDCl3
7.95 (d, J = 8.3 Hz, 1H), 7.31 (d, J = 8.3 Hz, 1H), 7.02 (d, J = 2.5 Hz, 1H), 6.82 (d, J = 8.6 Hz, 1H), 6.76 (dd, J = 8.6, 2.5 Hz, 1H), 6.16 (s, 1H), 4.33-4.19 (m, 4H), 4.05 (s, 3H)
null
[('d', ['8.3Hz'], '1H', 7.95, 7.95), ('d', ['8.3Hz'], '1H', 7.31, 7.31), ('d', ['2.5Hz'], '1H', 7.02, 7.02), ('d', ['8.6Hz'], '1H', 6.82, 6.82), ('dd', ['8.6Hz', '2.5Hz'], '1H', 6.76, 6.76), ('s', [], '1H', 6.16, 6.16), ('m', [], '4H', 4.33, 4.19), ('s', [], '3H', 4.05, 4.05)]
13
9
13
10.1021_acs.orglett.4c02707
C(F)(F)(F)c1ccc2c(Nc3ccc4c(c3)OCCO4)nn(C)c2n1
3
3
[0.11904872 0.45937502 0.32984837 0.57656252]
[0.11475184 0.59726565 0.8841453 0.69335945]
19F NMR
377 MHz
CDCl3
-66.9
null
[(-66.9, None, None)]
3
1
1
10.1021_acs.orglett.4c02707
Cn1nc(NC23CC4CC(CC(C4)C2)C3)c2ccc(Cl)nc21
4
4
[0.11879597 0.11367188 0.29572613 0.21328127]
[0.11525736 0.23496096 0.88465084 0.33066409]
1H NMR
400 MHz
DMSO-d6
8.26 (d, J = 8.2 Hz, 1H), 6.97 (d, J = 8.2 Hz, 1H), 5.97 (s, 1H), 3.73 (s, 3H), 2.06 (s, 9H), 1.66 (s, 6H)
null
[('d', ['8.2Hz'], '1H', 8.26, 8.26), ('d', ['8.2Hz'], '1H', 6.97, 6.97), ('s', [], '1H', 5.97, 5.97), ('s', [], '3H', 3.73, 3.73), ('s', [], '9H', 2.06, 2.06), ('s', [], '6H', 1.66, 1.66)]
21
7
21
10.1021_acs.orglett.4c02707
Cn1nc(NC23CC4CC(CC(C4)C2)C3)c2ccc(Cl)nc21
4
4
[0.11879597 0.11367188 0.29572613 0.21328127]
[0.11525736 0.23496096 0.88465084 0.33066409]
13C NMR
101 MHz
DMSO-d6
149.4, 149.0, 146.3, 133.2, 113.0, 106.7, 51.2, 41.3, 36.2, 33.0, 29.0
null
[(149.4, None, None), (149.0, None, None), (146.3, None, None), (133.2, None, None), (113.0, None, None), (106.7, None, None), (51.2, None, None), (41.3, None, None), (36.2, None, None), (33.0, None, None), (29.0, None, None)]
17
11
11
10.1021_acs.orglett.4c02707
c1(B2OC(C)(C)C(C)(C)O2)ccc(Nc2nn(C)c3ncc(Br)c(C)c23)cc1
4
4
[0.11879597 0.7179688 0.34273898 0.8117188 ]
[0.11449909 0.83359381 0.88465084 0.90859377]
1H NMR
400 MHz
CDCl3
8.51 (s, 1H), 7.68 (d, J = 8.5 Hz, 2H), 6.92 (d, J = 8.5 Hz, 2H), 6.09 (s, 1H), 4.04 (s, 3H), 2.53 (s, 3H), 1.33 (s, 12H)
null
[('s', [], '1H', 8.51, 8.51), ('d', ['8.5Hz'], '2H', 7.68, 7.68), ('d', ['8.5Hz'], '2H', 6.92, 6.92), ('s', [], '1H', 6.09, 6.09), ('s', [], '3H', 4.04, 4.04), ('s', [], '3H', 2.53, 2.53), ('s', [], '12H', 1.33, 1.33)]
24
7
24
10.1021_acs.orglett.4c02707
c1(B2OC(C)(C)C(C)(C)O2)ccc(Nc2nn(C)c3ncc(Br)c(C)c23)cc1
4
4
[0.11879597 0.7179688 0.34273898 0.8117188 ]
[0.11449909 0.83359381 0.88465084 0.90859377]
13C NMR
101 MHz
CDCl3
151.1, 149.8, 147.4, 141.7, 140.6, 136.5, 115.1, 114.6, 111.3, 83.6, 33.9, 25.0, 18.6
null
[(151.1, None, None), (149.8, None, None), (147.4, None, None), (141.7, None, None), (140.6, None, None), (136.5, None, None), (115.1, None, None), (114.6, None, None), (111.3, None, None), (83.6, None, None), (33.9, None, None), (25.0, None, None), (18.6, None, None)]
20
14
13
10.1021_acs.orglett.4c02707
Cn1nc(Nc2ccc(Br)cc2)c2cc(Cl)cnc21
5
5
[0.11930148 0.3042969 0.32605701 0.3980469 ]
[0.11525736 0.41953127 0.88465084 0.5148438 ]
1H NMR
400 MHz
DMSO-d6
9.35 (s, 1H), 8.65-8.33 (m, 2H), 7.63 (d, J = 8.9 Hz, 2H), 7.46 (d, J = 8.9 Hz, 2H), 3.92 (s, 3H)
null
[('s', [], '1H', 9.35, 9.35), ('m', [], '2H', 8.65, 8.33), ('d', ['8.9Hz'], '2H', 7.63, 7.63), ('d', ['8.9Hz'], '2H', 7.46, 7.46), ('s', [], '3H', 3.92, 3.92)]
10
6
10
10.1021_acs.orglett.4c02707
Cn1nc(Nc2ccc(Br)cc2)c2cc(Cl)cnc21
5
5
[0.11930148 0.3042969 0.32605701 0.3980469 ]
[0.11525736 0.41953127 0.88465084 0.5148438 ]
13C NMR
101 MHz
DMSO-d6
148.0, 148.0, 142.0, 141.1, 131.5, 128.9, 121.0, 117.9, 110.7, 107.3, 33.3
null
[(148.0, None, None), (148.0, None, None), (142.0, None, None), (141.1, None, None), (131.5, None, None), (128.9, None, None), (121.0, None, None), (117.9, None, None), (110.7, None, None), (107.3, None, None), (33.3, None, None)]
13
11
11
10.1021_acs.orglett.4c02707
Cn1nc(Nc2cnc3ccccc3c2)c2ccc(Cl)nc21
5
5
[0.11904872 0.68984377 0.32352944 0.8039063 ]
[0.11500461 0.82500003 0.88363977 0.88125002]
1H NMR
400 MHz
DMSO-d6
9.90 (s, 1H), 8.97 (d, J = 2.7 Hz, 1H), 8.76 (d, J = 2.7 Hz, 1H), 8.48 (d, J = 8.3 Hz, 1H), 7.96-7.82 (m, 2H), 7.58-7.49 (m, 2H), 7.24 (d, J = 8.3 Hz, 1H), 3.98 (s, 3H)
null
[('s', [], '1H', 9.9, 9.9), ('d', ['2.7Hz'], '1H', 8.97, 8.97), ('d', ['2.7Hz'], '1H', 8.76, 8.76), ('d', ['8.3Hz'], '1H', 8.48, 8.48), ('m', [], '2H', 7.96, 7.82), ('m', [], '2H', 7.58, 7.49), ('d', ['8.3Hz'], '1H', 7.24, 7.24), ('s', [], '3H', 3.98, 3.98)]
12
10
12
10.1021_acs.orglett.4c02707
Cn1nc(Nc2cnc3ccccc3c2)c2ccc(Cl)nc21
5
5
[0.11904872 0.68984377 0.32352944 0.8039063 ]
[0.11500461 0.82500003 0.88363977 0.88125002]
13C NMR
101 MHz
DMSO-d6
150.4, 148.9, 143.7, 142.7, 142.5, 135.5, 133.1, 128.60, 128.56, 127.03, 126.96, 126.1, 115.8, 115.0, 105.9, 33.5
null
[(150.4, None, None), (148.9, None, None), (143.7, None, None), (142.7, None, None), (142.5, None, None), (135.5, None, None), (133.1, None, None), (128.6, None, None), (128.56, None, None), (127.03, None, None), (126.96, None, None), (126.1, None, None), (115.8, None, None), (115.0, None, None), (105.9, None, None), (...
16
16
16
10.1021_acs.orglett.4c02707
Cc1ccnc2c1c(Nc1ccc(Br)cc1)nn2C
6
6
[0.11879597 0.32460939 0.29319855 0.41679691]
[0.11601563 0.43867188 0.88465084 0.53476565]
1H NMR
400 MHz
DMSO-d6
8.34 (d, J = 4.6 Hz, 1H), 8.26 (s, 1H), 7.35 (d, J = 8.9 Hz, 2H), 7.17 (d, J = 8.9 Hz, 2H), 6.89 (d, J = 4.6 Hz, 1H), 3.94 (s, 3H), 2.58 (s, 3H)
null
[('d', ['4.6Hz'], '1H', 8.34, 8.34), ('s', [], '1H', 8.26, 8.26), ('d', ['8.9Hz'], '2H', 7.35, 7.35), ('d', ['8.9Hz'], '2H', 7.17, 7.17), ('d', ['4.6Hz'], '1H', 6.89, 6.89), ('s', [], '3H', 3.94, 3.94), ('s', [], '3H', 2.58, 2.58)]
13
7
13
10.1021_acs.orglett.4c02707
Cc1ccnc2c1c(Nc1ccc(Br)cc1)nn2C
6
6
[0.11879597 0.32460939 0.29319855 0.41679691]
[0.11601563 0.43867188 0.88465084 0.53476565]
13C NMR
101 MHz
DMSO-d6
150.4, 149.2, 144.1, 142.6, 141.5, 131.4, 117.3, 117.1, 109.8, 108.7, 33.2, 18.3
null
[(150.4, None, None), (149.2, None, None), (144.1, None, None), (142.6, None, None), (141.5, None, None), (131.4, None, None), (117.3, None, None), (117.1, None, None), (109.8, None, None), (108.7, None, None), (33.2, None, None), (18.3, None, None)]
14
12
12
10.1021_acs.orglett.4c02707
COC(=O)C(Cc1c[nH]c2ccccc12)Nc1nn(C)c2nc(C)c(Cl)cc12
6
6
[0.11879597 0.74218758 0.34728862 0.85000002]
[0.11525736 0.87187503 0.8826287 0.90781256]
1H NMR
400 MHz
DMSO-d6
10.84 (s, 1H), 8.31 (s, 1H), 7.55 (d, J = 7.8 Hz, 1H), 7.33 (d, J = 8.1 Hz, 1H), 7.19 (d, J = 2.4 Hz, 1H), 7.06 (ddd, J = 8.1, 7.0, 1.0 Hz, 1H), 6.99 (ddd, J = 8.1, 7.0, 1.0 Hz, 1H), 6.87 (d, J = 8.8 Hz, 1H), 4.52 (td, J = 8.2, 6.0 Hz, 1H), 3.69 (s, 3H), 3.57 (s, 3H), 3.25 (dd, J = 14.6, 5.8 Hz, 1H), 3.17 (dd, J = 14.6...
null
[('s', [], '1H', 10.84, 10.84), ('s', [], '1H', 8.31, 8.31), ('d', ['7.8Hz'], '1H', 7.55, 7.55), ('d', ['8.1Hz'], '1H', 7.33, 7.33), ('d', ['2.4Hz'], '1H', 7.19, 7.19), ('ddd', ['8.1Hz', '7.0Hz', '1.0Hz'], '1H', 7.06, 7.06), ('ddd', ['8.1Hz', '7.0Hz', '1.0Hz'], '1H', 6.99, 6.99), ('d', ['8.8Hz'], '1H', 6.87, 6.87), ('t...
20
13
20
10.1021_acs.orglett.4c02707
COC(=O)C(Cc1c[nH]c2ccccc12)Nc1nn(C)c2nc(C)c(Cl)cc12
6
6
[0.11879597 0.74218758 0.34728862 0.85000002]
[0.11525736 0.87187503 0.8826287 0.90781256]
13C NMR
101 MHz
DMSO-d6
173.9, 154.6, 148.8, 145.9, 136.1, 129.7, 127.1, 123.8, 120.9, 119.9, 118.4, 118.1, 111.4, 109.8, 105.2, 56.4, 51.7, 32.9, 28.0, 23.3
null
[(173.9, None, None), (154.6, None, None), (148.8, None, None), (145.9, None, None), (136.1, None, None), (129.7, None, None), (127.1, None, None), (123.8, None, None), (120.9, None, None), (119.9, None, None), (118.4, None, None), (118.1, None, None), (111.4, None, None), (109.8, None, None), (105.2, None, None), (56....
20
20
20
10.1021_acs.orglett.4c02707
COC(=O)c1ccc(Nc2nn(C)c3ncc(C(=O)OC)cc23)cc1
7
7
[0.11904872 0.38339846 0.36624542 0.48984377]
[0.11525736 0.51171879 0.8856618 0.60703127]
1H NMR
400 MHz
DMSO-d6
9.99 (s, 1H), 9.15 (d, J = 2.0 Hz, 1H), 9.02 (d, J = 2.0 Hz, 1H), 7.94 (d, J = 8.9 Hz, 2H), 7.81 (d, J = 8.9 Hz, 2H), 3.99 (s, 3H), 3.92 (s, 3H), 3.82 (s, 3H)
null
[('s', [], '1H', 9.99, 9.99), ('d', ['2.0Hz'], '1H', 9.15, 9.15), ('d', ['2.0Hz'], '1H', 9.02, 9.02), ('d', ['8.9Hz'], '2H', 7.94, 7.94), ('d', ['8.9Hz'], '2H', 7.81, 7.81), ('s', [], '3H', 3.99, 3.99), ('s', [], '3H', 3.92, 3.92), ('s', [], '3H', 3.82, 3.82)]
16
8
16
10.1021_acs.orglett.4c02707
COC(=O)c1ccc(Nc2nn(C)c3ncc(C(=O)OC)cc23)cc1
7
7
[0.11904872 0.38339846 0.36624542 0.48984377]
[0.11525736 0.51171879 0.8856618 0.60703127]
13C NMR
101 MHz
DMSO-d6
166.0, 165.6, 150.6, 150.4, 145.8, 143.5, 132.7, 130.7, 120.5, 116.8, 115.6, 106.7, 52.2, 51.6, 33.5
null
[(166.0, None, None), (165.6, None, None), (150.6, None, None), (150.4, None, None), (145.8, None, None), (143.5, None, None), (132.7, None, None), (130.7, None, None), (120.5, None, None), (116.8, None, None), (115.6, None, None), (106.7, None, None), (52.2, None, None), (51.6, None, None), (33.5, None, None)]
17
15
15
10.1021_acs.orglett.4c02707
O(C)c1cc2c(cn1)c(Nc1ccc(B3OC(C)(C)C(C)(C)O3)cc1)nn2C
8
8
[0.11803769 0.09218751 0.34905791 0.19218751]
[0.11525736 0.19824221 0.88465084 0.31308596]
1H NMR
400 MHz
DMSO-d6
9.46 (s, 1H), 8.87 (d, J = 1.0 Hz, 1H), 7.69 (d, J = 8.6 Hz, 2H), 7.62 (d, J = 8.6 Hz, 2H), 6.73 (d, J = 0.9 Hz, 1H), 3.91 (s, 3H), 3.82 (s, 3H), 1.29 (s, 12H)
null
[('s', [], '1H', 9.46, 9.46), ('d', ['1.0Hz'], '1H', 8.87, 8.87), ('d', ['8.6Hz'], '2H', 7.69, 7.69), ('d', ['8.6Hz'], '2H', 7.62, 7.62), ('d', ['0.9Hz'], '1H', 6.73, 6.73), ('s', [], '3H', 3.91, 3.91), ('s', [], '3H', 3.82, 3.82), ('s', [], '12H', 1.29, 1.29)]
25
8
25
10.1021_acs.orglett.4c02707
O(C)c1cc2c(cn1)c(Nc1ccc(B3OC(C)(C)C(C)(C)O3)cc1)nn2C
8
8
[0.11803769 0.09218751 0.34905791 0.19218751]
[0.11525736 0.19824221 0.88465084 0.31308596]
13C NMR
101 MHz
DMSO-d6
162.7, 145.8, 144.7, 144.0, 141.7, 135.5, 118.7, 115.4, 110.7, 84.8, 83.2, 54.1, 34.8, 24.7
null
[(162.7, None, None), (145.8, None, None), (144.7, None, None), (144.0, None, None), (141.7, None, None), (135.5, None, None), (118.7, None, None), (115.4, None, None), (110.7, None, None), (84.8, None, None), (83.2, None, None), (54.1, None, None), (34.8, None, None), (24.7, None, None)]
20
14
14
10.1021_acs.orglett.4c02707
Cc1cc2c(cn1)c(Nc1ccc(B3OC(C)(C)C(C)(C)O3)cc1)nn2C
8
8
[0.11879597 0.49453127 0.38267465 0.6085938 ]
[0.11500461 0.6484375 0.88363977 0.76328131]
1H NMR
400 MHz
DMSO-d6
9.46 (s, 1H), 9.08 (s, 1H), 7.69 (d, J = 8.5 Hz, 2H), 7.61 (d, J = 8.4 Hz, 2H), 7.29 (s, 1H), 3.87 (s, 3H), 2.54 (s, 3H), 1.28 (s, 12H)
null
[('s', [], '1H', 9.46, 9.46), ('s', [], '1H', 9.08, 9.08), ('d', ['8.5Hz'], '2H', 7.69, 7.69), ('d', ['8.4Hz'], '2H', 7.61, 7.61), ('s', [], '1H', 7.29, 7.29), ('s', [], '3H', 3.87, 3.87), ('s', [], '3H', 2.54, 2.54), ('s', [], '12H', 1.28, 1.28)]
25
8
25
10.1021_acs.orglett.4c02707
Cc1cc2c(cn1)c(Nc1ccc(B3OC(C)(C)C(C)(C)O3)cc1)nn2C
8
8
[0.11879597 0.49453127 0.38267465 0.6085938 ]
[0.11500461 0.6484375 0.88363977 0.76328131]
13C NMR
101 MHz
DMSO-d6
153.0, 144.8, 143.9, 143.44, 143.39, 135.6, 118.6 (br), 115.2, 111.2, 101.6, 83.2, 34.8, 24.7, 24.2
null
[(153.0, None, None), (144.8, None, None), (143.9, None, None), (143.44, None, None), (143.39, None, None), (135.6, None, None), (118.6, None, None), (115.2, None, None), (111.2, None, None), (101.6, None, None), (83.2, None, None), (34.8, None, None), (24.7, None, None), (24.2, None, None)]
20
14
14
10.1021_acs.orglett.4c02707
Cn1nc(NC23CC4CC(CC(C4)C2)C3)c2cnccc21
9
9
[0.11879597 0.11328126 0.26135112 0.21171876]
[0.11525736 0.23320314 0.88465084 0.32929688]
1H NMR
400 MHz
DMSO-d6
8.99 (d, J = 1.1 Hz, 1H), 8.16 (d, J = 6.0 Hz, 1H), 7.26 (dd, J = 6.0, 1.1 Hz, 1H), 5.96 (s, 1H), 3.75 (s, 3H), 2.08 (s, 9H), 1.66 (s, 6H)
null
[('d', ['1.1Hz'], '1H', 8.99, 8.99), ('d', ['6.0Hz'], '1H', 8.16, 8.16), ('dd', ['6.0Hz', '1.1Hz'], '1H', 7.26, 7.26), ('s', [], '1H', 5.96, 5.96), ('s', [], '3H', 3.75, 3.75), ('s', [], '9H', 2.08, 2.08), ('s', [], '6H', 1.66, 1.66)]
22
8
22
10.1021_acs.orglett.4c02707
Cn1nc(NC23CC4CC(CC(C4)C2)C3)c2cnccc21
9
9
[0.11879597 0.11328126 0.26135112 0.21171876]
[0.11525736 0.23320314 0.88465084 0.32929688]
13C NMR
101 MHz
DMSO-d6
147.6, 144.4, 143.8, 142.2, 113.2, 103.1, 51.2, 41.3, 36.2, 34.6, 29.0
null
[(147.6, None, None), (144.4, None, None), (143.8, None, None), (142.2, None, None), (113.2, None, None), (103.1, None, None), (51.2, None, None), (41.3, None, None), (36.2, None, None), (34.6, None, None), (29.0, None, None)]
17
11
11
10.1021_acs.orglett.4c02707
Cn1nc(NCCN2CCOCC2)c2cncc(Cl)c21
9
9
[0.11879597 0.53671877 0.30785849 0.6242188 ]
[0.11525736 0.6789063 0.88363977 0.77421878]
1H NMR
400 MHz
DMSO-d6
8.89 (s, 1H), 8.20 (s, 1H), 6.61 (t, J = 5.6 Hz, 1H), 4.02 (s, 3H), 3.62-3.55 (m, 4H), 3.42-3.33 (m, 2H), 2.56 (t, J = 6.8 Hz, 2H), 2.46-2.39 (m, 4H)
null
[('s', [], '1H', 8.89, 8.89), ('s', [], '1H', 8.2, 8.2), ('t', ['5.6Hz'], '1H', 6.61, 6.61), ('s', [], '3H', 4.02, 4.02), ('m', [], '4H', 3.62, 3.55), ('m', [], '2H', 3.42, 3.33), ('t', ['6.8Hz'], '2H', 2.56, 2.56), ('m', [], '4H', 2.46, 2.39)]
18
8
18
10.1021_acs.orglett.4c02707
Cn1nc(NCCN2CCOCC2)c2cncc(Cl)c21
9
9
[0.11879597 0.53671877 0.30785849 0.6242188 ]
[0.11525736 0.6789063 0.88363977 0.77421878]
13C NMR
101 MHz
DMSO-d6
149.3, 143.6, 143.2, 138.7, 114.2, 111.4, 66.2, 57.3, 53.5, 40.1, 36.9
null
[(149.3, None, None), (143.6, None, None), (143.2, None, None), (138.7, None, None), (114.2, None, None), (111.4, None, None), (66.2, None, None), (57.3, None, None), (53.5, None, None), (40.1, None, None), (36.9, None, None)]
13
11
11
10.1021_acs.orglett.4c02707
Cc1ccnc(Cl)c1Nc1nn(C)c2ccc(Br)nc12
10
10
[0.11904872 0.16435548 0.29395681 0.2730469 ]
[0.11601563 0.27968752 0.88465084 0.37578128]
1H NMR
400 MHz
DMSO-d6
8.34 (s, 1H), 8.12 (d, J = 4.9 Hz, 1H), 7.96 (d, J = 8.9 Hz, 1H), 7.53 (d, J = 8.8 Hz, 1H), 7.34 (dd, J = 4.9, 0.7 Hz, 1H), 3.77 (s, 3H), 2.25 (s, 3H)
null
[('s', [], '1H', 8.34, 8.34), ('d', ['4.9Hz'], '1H', 8.12, 8.12), ('d', ['8.9Hz'], '1H', 7.96, 7.96), ('d', ['8.8Hz'], '1H', 7.53, 7.53), ('dd', ['4.9Hz', '0.7Hz'], '1H', 7.34, 7.34), ('s', [], '3H', 3.77, 3.77), ('s', [], '3H', 2.25, 2.25)]
11
7
11
10.1021_acs.orglett.4c02707
Cc1ccnc(Cl)c1Nc1nn(C)c2ccc(Br)nc12
10
10
[0.11904872 0.16435548 0.29395681 0.2730469 ]
[0.11601563 0.27968752 0.88465084 0.37578128]
13C NMR
101 MHz
DMSO-d6
148.8, 147.7, 145.2, 144.7, 134.5, 133.1, 132.3, 130.7, 125.3, 125.0, 120.9, 35.4, 18.2
null
[(148.8, None, None), (147.7, None, None), (145.2, None, None), (144.7, None, None), (134.5, None, None), (133.1, None, None), (132.3, None, None), (130.7, None, None), (125.3, None, None), (125.0, None, None), (120.9, None, None), (35.4, None, None), (18.2, None, None)]
13
13
13
10.1021_acs.orglett.4c02707
COC(=O)C(Cc1c[nH]c2ccccc12)Nc1nn(C)c2cc(Cl)cnc12
10
10
[0.1185432 0.54882816 0.34349726 0.65664064]
[0.11475184 0.6632813 0.88313423 0.75859378]
1H NMR
400 MHz
DMSO-d6
10.85 (d, J = 2.5 Hz, 1H), 8.24 (d, J = 2.0 Hz, 1H), 8.10 (d, J = 2.0 Hz, 1H), 7.54 (d, J = 7.8 Hz, 1H), 7.33 (d, J = 8.1 Hz, 1H), 7.22 (d, J = 2.4 Hz, 1H), 7.06 (ddd, J = 8.1, 6.9, 1.3 Hz, 1H), 6.98 (ddd, J = 8.0, 7.0, 1.1 Hz, 1H), 6.31 (d, J = 8.8 Hz, 1H), 4.76-4.53 (m, 1H), 3.73 (s, 3H), 3.59 (s, 3H), 3.29 (d, J = 6...
null
[('d', ['2.5Hz'], '1H', 10.85, 10.85), ('d', ['2.0Hz'], '1H', 8.24, 8.24), ('d', ['2.0Hz'], '1H', 8.1, 8.1), ('d', ['7.8Hz'], '1H', 7.54, 7.54), ('d', ['8.1Hz'], '1H', 7.33, 7.33), ('d', ['2.4Hz'], '1H', 7.22, 7.22), ('ddd', ['8.1Hz', '6.9Hz', '1.3Hz'], '1H', 7.06, 7.06), ('ddd', ['8.0Hz', '7.0Hz', '1.1Hz'], '1H', 6.98...
18
13
18
10.1021_acs.orglett.4c02707
COC(=O)C(Cc1c[nH]c2ccccc12)Nc1nn(C)c2cc(Cl)cnc12
10
10
[0.1185432 0.54882816 0.34349726 0.65664064]
[0.11475184 0.6632813 0.88313423 0.75859378]
13C NMR
101 MHz
DMSO-d6
173.7, 147.8, 140.1, 136.1, 134.1, 129.6, 128.8, 127.2, 124.0, 120.9, 118.4, 118.1, 116.4, 111.4, 109.8, 56.6, 51.7, 35.1, 27.6
null
[(173.7, None, None), (147.8, None, None), (140.1, None, None), (136.1, None, None), (134.1, None, None), (129.6, None, None), (128.8, None, None), (127.2, None, None), (124.0, None, None), (120.9, None, None), (118.4, None, None), (118.1, None, None), (116.4, None, None), (111.4, None, None), (109.8, None, None), (56....
19
19
19
10.1021_acs.orglett.4c02707
Cn1nc(Nc2ccc3c(c2)OCCO3)c2ncccc21
11
11
[0.1185432 0.14589844 0.29016545 0.26113283]
[0.11424633 0.26796877 0.88363977 0.36328129]
1H NMR
400 MHz
DMSO-d6
8.91 (s, 1H), 8.38 (d, J = 4.3 Hz, 1H), 7.95 (d, J = 9.8 Hz, 1H), 7.49 (d, J = 2.6 Hz, 1H), 7.40 (dd, J = 8.5, 4.3 Hz, 1H), 7.25 (dd, J = 8.8, 2.6 Hz, 1H), 6.76 (d, J = 8.8 Hz, 1H), 4.27-4.11 (m, 4H), 3.91 (s, 3H)
null
[('s', [], '1H', 8.91, 8.91), ('d', ['4.3Hz'], '1H', 8.38, 8.38), ('d', ['9.8Hz'], '1H', 7.95, 7.95), ('d', ['2.6Hz'], '1H', 7.49, 7.49), ('dd', ['8.5Hz', '4.3Hz'], '1H', 7.4, 7.4), ('dd', ['8.8Hz', '2.6Hz'], '1H', 7.25, 7.25), ('d', ['8.8Hz'], '1H', 6.76, 6.76), ('m', [], '4H', 4.27, 4.11), ('s', [], '3H', 3.91, 3.91)...
14
10
14
10.1021_acs.orglett.4c02707
Cn1nc(Nc2ccc3c(c2)OCCO3)c2ncccc21
11
11
[0.1185432 0.14589844 0.29016545 0.26113283]
[0.11424633 0.26796877 0.88363977 0.36328129]
13C NMR
101 MHz
DMSO-d6
144.5, 143.0, 141.8, 136.51, 136.49, 133.1, 131.9, 121.6, 117.0, 116.7, 109.8, 105.1, 64.3, 63.9, 35.2
null
[(144.5, None, None), (143.0, None, None), (141.8, None, None), (136.51, None, None), (136.49, None, None), (133.1, None, None), (131.9, None, None), (121.6, None, None), (117.0, None, None), (116.7, None, None), (109.8, None, None), (105.1, None, None), (64.3, None, None), (63.9, None, None), (35.2, None, None)]
15
15
15
10.1021_acs.orglett.4c02707
Cn1nc(Nc2cnc3ccccc3c2)c2nc(Br)ccc21
11
11
[0.11904872 0.55820315 0.32378218 0.67304692]
[0.11525736 0.67968758 0.88465084 0.77578127]
1H NMR
400 MHz
DMSO-d6
9.89 (s, 1H), 9.19 (d, J = 2.7 Hz, 1H), 8.76 (d, J = 2.6 Hz, 1H), 8.09 (d, J = 8.8 Hz, 1H), 7.94-7.78 (m, 2H), 7.63 (d, J = 8.8 Hz, 1H), 7.61-7.47 (m, 2H), 4.04 (s, 3H)
null
[('s', [], '1H', 9.89, 9.89), ('d', ['2.7Hz'], '1H', 9.19, 9.19), ('d', ['2.6Hz'], '1H', 8.76, 8.76), ('d', ['8.8Hz'], '1H', 8.09, 8.09), ('m', [], '2H', 7.94, 7.78), ('d', ['8.8Hz'], '1H', 7.63, 7.63), ('m', [], '2H', 7.61, 7.47), ('s', [], '3H', 4.04, 4.04)]
12
10
12
10.1021_acs.orglett.4c02707
S(C)c1ncc2c(Nc3c(C)cccc3C)nn(C)c2n1
12
12
[0.11904872 0.14511719 0.30735295 0.25292971]
[0.11626839 0.25976564 0.88465084 0.35546879]
1H NMR
400 MHz
DMSO-d6
8.46 (s, 1H), 8.32 (s, 1H), 7.16-7.05 (m, 3H), 3.67 (s, 3H), 2.54 (s, 3H), 2.18 (s, 6H)
null
[('s', [], '1H', 8.46, 8.46), ('s', [], '1H', 8.32, 8.32), ('m', [], '3H', 7.16, 7.05), ('s', [], '3H', 3.67, 3.67), ('s', [], '3H', 2.54, 2.54), ('s', [], '6H', 2.18, 2.18)]
17
7
17
10.1021_acs.orglett.4c02707
S(C)c1ncc2c(Nc3c(C)cccc3C)nn(C)c2n1
12
12
[0.11904872 0.14511719 0.30735295 0.25292971]
[0.11626839 0.25976564 0.88465084 0.35546879]
13C NMR
101 MHz
DMSO-d6
169.0, 152.2, 151.1, 146.6, 137.6, 135.4, 128.2, 125.9, 102.9, 32.4, 18.2, 13.6
null
[(169.0, None, None), (152.2, None, None), (151.1, None, None), (146.6, None, None), (137.6, None, None), (135.4, None, None), (128.2, None, None), (125.9, None, None), (102.9, None, None), (32.4, None, None), (18.2, None, None), (13.6, None, None)]
15
12
12
10.1021_acs.orglett.4c02707
Cc1ncnc2c1c(Nc1ccc(Br)cc1)nn2C
12
12
[0.11904872 0.53710941 0.29800093 0.63007817]
[0.11601563 0.63671879 0.88465084 0.73203131]
1H NMR
400 MHz
DMSO-d6
8.73 (s, 1H), 8.53 (s, 1H), 7.50-7.37 (m, 4H), 3.90 (s, 3H), 2.77 (s, 3H)
null
[('s', [], '1H', 8.73, 8.73), ('s', [], '1H', 8.53, 8.53), ('m', [], '4H', 7.5, 7.37), ('s', [], '3H', 3.9, 3.9), ('s', [], '3H', 2.77, 2.77)]
12
6
12
10.1021_acs.orglett.4c02707
Cc1ncnc2c1c(Nc1ccc(Br)cc1)nn2C
12
12
[0.11904872 0.53710941 0.29800093 0.63007817]
[0.11601563 0.63671879 0.88465084 0.73203131]
13C NMR
101 MHz
DMSO-d6
162.5, 155.3, 151.7, 142.8, 142.2, 131.4, 118.6, 111.1, 106.1, 33.1, 22.4
null
[(162.5, None, None), (155.3, None, None), (151.7, None, None), (142.8, None, None), (142.2, None, None), (131.4, None, None), (118.6, None, None), (111.1, None, None), (106.1, None, None), (33.1, None, None), (22.4, None, None)]
13
11
11
10.1021_acs.orglett.4c02707
Cn1nc(NCCN2CCOCC2)c2c(Cl)ncnc21
13
13
[0.11904872 0.11367188 0.29951749 0.2263672 ]
[0.11424633 0.23300782 0.88363977 0.32871096]
1H NMR
400 MHz
DMSO-d6
8.14 (s, 1H), 6.52 (s, 1H), 3.89 (t, J = 5.6 Hz, 2H), 3.75-3.62 (m, 8H), 3.65 (s, 3H), 3.57 (dd, J = 6.2, 5.0 Hz, 2H)
null
[('s', [], '1H', 8.14, 8.14), ('s', [], '1H', 6.52, 6.52), ('t', ['5.6Hz'], '2H', 3.89, 3.89), ('m', [], '8H', 3.75, 3.62), ('s', [], '3H', 3.65, 3.65), ('dd', ['6.2Hz', '5.0Hz'], '2H', 3.57, 3.57)]
17
7
17
10.1021_acs.orglett.4c02707
Cn1nc(NCCN2CCOCC2)c2c(Cl)ncnc21
13
13
[0.11904872 0.11367188 0.29951749 0.2263672 ]
[0.11424633 0.23300782 0.88363977 0.32871096]
13C NMR
101 MHz
DMSO-d6
157.4, 155.7, 152.9, 150.3, 90.8, 70.3, 68.3, 54.9, 48.2, 45.0, 43.7, 32.5
null
[(157.4, None, None), (155.7, None, None), (152.9, None, None), (150.3, None, None), (90.8, None, None), (70.3, None, None), (68.3, None, None), (54.9, None, None), (48.2, None, None), (45.0, None, None), (43.7, None, None), (32.5, None, None)]
12
10
12
10.1021_acs.orglett.4c02707
S(C)c1ncc2cc3c(NC45CC6CC(CC(C6)C4)C5)nn(C)c3nc2n1
13
13
[0.11879597 0.52578127 0.34273898 0.6242188 ]
[0.11500461 0.63046877 0.88363977 0.7257813 ]
1H NMR
400 MHz
DMSO-d6
9.26 (s, 1H), 8.98 (s, 1H), 6.69 (s, 1H), 3.81 (s, 3H), 2.61 (s, 3H), 2.20-2.03 (m, 9H), 1.68 (s, 6H)
null
[('s', [], '1H', 9.26, 9.26), ('s', [], '1H', 8.98, 8.98), ('s', [], '1H', 6.69, 6.69), ('s', [], '3H', 3.81, 3.81), ('s', [], '3H', 2.61, 2.61), ('m', [], '9H', 2.2, 2.03), ('s', [], '6H', 1.68, 1.68)]
24
8
24
10.1021_acs.orglett.4c02707
S(C)c1ncc2cc3c(NC45CC6CC(CC(C6)C4)C5)nn(C)c3nc2n1
13
13
[0.11879597 0.52578127 0.34273898 0.6242188 ]
[0.11500461 0.63046877 0.88363977 0.7257813 ]
13C NMR
101 MHz
DMSO-d6
172.2, 162.6, 157.1, 151.6, 147.7, 133.8, 112.1, 111.4, 51.4, 40.8, 36.2, 33.0, 29.0, 13.9
null
[(172.2, None, None), (162.6, None, None), (157.1, None, None), (151.6, None, None), (147.7, None, None), (133.8, None, None), (112.1, None, None), (111.4, None, None), (51.4, None, None), (40.8, None, None), (36.2, None, None), (33.0, None, None), (29.0, None, None), (13.9, None, None)]
20
14
14
10.1021_acs.orglett.4c02707
COc1ccc(Nc2nn(C)c3nc(C)cnc23)cc1
14
14
[0.11904872 0.11367188 0.34602483 0.20625001]
[0.11525736 0.21269532 0.88465084 0.30839845]
1H NMR
400 MHz
DMSO-d6
9.18 (s, 1H), 8.37 (s, 1H), 7.77-7.68 (m, 2H), 6.93-6.84 (m, 2H), 3.88 (s, 3H), 3.71 (s, 3H), 2.63 (s, 3H)
null
[('s', [], '1H', 9.18, 9.18), ('s', [], '1H', 8.37, 8.37), ('m', [], '2H', 7.77, 7.68), ('m', [], '2H', 6.93, 6.84), ('s', [], '3H', 3.88, 3.88), ('s', [], '3H', 3.71, 3.71), ('s', [], '3H', 2.63, 2.63)]
15
7
15
10.1021_acs.orglett.4c02707
COc1ccc(Nc2nn(C)c3nc(C)cnc23)cc1
14
14
[0.11904872 0.11367188 0.34602483 0.20625001]
[0.11525736 0.21269532 0.88465084 0.30839845]
13C NMR
101 MHz
DMSO-d6
153.2, 152.9, 143.4, 142.7, 137.6, 135.5, 123.2, 117.8, 114.0, 55.2, 33.1, 21.7
null
[(153.2, None, None), (152.9, None, None), (143.4, None, None), (142.7, None, None), (137.6, None, None), (135.5, None, None), (123.2, None, None), (117.8, None, None), (114.0, None, None), (55.2, None, None), (33.1, None, None), (21.7, None, None)]
14
12
12
10.1021_acs.orglett.4c02707
c1(-c2ccccc2)ccccc1Nc1nn(C)c2cc(F)ccc12
14
14
[0.11930148 0.4992188 0.28637409 0.6085938 ]
[0.11576287 0.61484377 0.88313423 0.7101563 ]
1H NMR
400 MHz
DMSO-d6
7.77 (dd, J = 8.1, 1.2 Hz, 1H), 7.54-7.46 (m, 4H), 7.46-7.39 (m, 2H), 7.38-7.26 (m, 3H), 7.23 (dd, J = 7.6, 1.6 Hz, 1H), 7.04 (td, J = 7.4, 1.2 Hz, 1H), 6.82 (td, J = 9.2, 2.2 Hz, 1H), 3.80 (s, 3H)
null
[('dd', ['8.1Hz', '1.2Hz'], '1H', 7.77, 7.77), ('m', [], '4H', 7.54, 7.46), ('m', [], '2H', 7.46, 7.39), ('m', [], '3H', 7.38, 7.26), ('dd', ['7.6Hz', '1.6Hz'], '1H', 7.23, 7.23), ('td', ['7.4Hz', '1.2Hz'], '1H', 7.04, 7.04), ('td', ['9.2Hz', '2.2Hz'], '1H', 6.82, 6.82), ('s', [], '3H', 3.8, 3.8)]
16
12
16
10.1021_acs.orglett.4c02707
c1(-c2ccccc2)ccccc1Nc1nn(C)c2cc(F)ccc12
14
14
[0.11930148 0.4992188 0.28637409 0.6085938 ]
[0.11576287 0.61484377 0.88313423 0.7101563 ]
19F NMR
377 MHz
DMSO-d6
-114.9
null
[(-114.9, None, None)]
1
1
1
10.1021_acs.orglett.4c02707
C(F)(F)(F)c1ccc2c(Nc3c(C)cccc3C)nn(C)c2c1
15
15
[0.11904872 0.16269532 0.30305608 0.27089845]
[0.11626839 0.27734377 0.88465084 0.37265627]
1H NMR
400 MHz
DMSO-d6
7.89-7.78 (m, 3H), 7.20 (dd, J = 8.4, 1.5 Hz, 1H), 7.13-7.00 (m, 3H), 3.80 (s, 3H), 2.17 (s, 6H)
null
[('m', [], '3H', 7.89, 7.78), ('dd', ['8.4Hz', '1.5Hz'], '1H', 7.2, 7.2), ('m', [], '3H', 7.13, 7.0), ('s', [], '3H', 3.8, 3.8), ('s', [], '6H', 2.17, 2.17)]
16
8
16
10.1021_acs.orglett.4c02707
C(F)(F)(F)c1ccc2c(Nc3c(C)cccc3C)nn(C)c2c1
15
15
[0.11904872 0.16269532 0.30305608 0.27089845]
[0.11626839 0.27734377 0.88465084 0.37265627]
19F NMR
377 MHz
DMSO-d6
-59.90
null
[(-59.9, None, None)]
3
1
1
10.1021_acs.orglett.4c02707
Cc1ncnc2c1c(N[C@H]1CCCN(C(=O)OC(C)(C)C)C1)nn2C
15
15
[0.11930148 0.62031255 0.29597887 0.71328127]
[0.11424633 0.72031256 0.88313423 0.81562505]
1H NMR
400 MHz
DMSO-d6
8.60 (s, 1H), 5.65 (d, J = 6.3 Hz, 1H), 3.95 (m, 1H), 3.76 (s, 3H), 3.71-3.50 (m, 2H), 3.08 (m, 2H), 2.70 (s, 3H), 2.02 (br s, 1H), 1.83-1.54 (m, 2H), 1.49-1.17 (m, 10H)
null
[('s', [], '1H', 8.6, 8.6), ('d', ['6.3Hz'], '1H', 5.65, 5.65), ('m', [], '1H', 3.95, 3.95), ('s', [], '3H', 3.76, 3.76), ('m', [], '2H', 3.71, 3.5), ('m', [], '2H', 3.08, 3.08), ('s', [], '3H', 2.7, 2.7), ('brs', [], '1H', 2.02, 2.02), ('m', [], '2H', 1.83, 1.54), ('m', [], '10H', 1.49, 1.17)]
26
10
26
10.1021_acs.orglett.4c02707
Cc1ncnc2c1c(N[C@H]1CCCN(C(=O)OC(C)(C)C)C1)nn2C
15
15
[0.11930148 0.62031255 0.29597887 0.71328127]
[0.11424633 0.72031256 0.88313423 0.81562505]
13C NMR
101 MHz
DMSO-d6
162.1, 155.1, 154.0, 152.0, 147.4, 104.8, 78.3, 48.8, 47.3, 43.3, 32.6, 29.7, 27.9, 22.7, 22.3
null
[(162.1, None, None), (155.1, None, None), (154.0, None, None), (152.0, None, None), (147.4, None, None), (104.8, None, None), (78.3, None, None), (48.8, None, None), (47.3, None, None), (43.3, None, None), (32.6, None, None), (29.7, None, None), (27.9, None, None), (22.7, None, None), (22.3, None, None)]
17
15
15
10.1021_acs.orglett.4c02707
COc1ccc(Cn2nc(Nc3ccc4c(c3)OCCO4)c3ccc(C(F)(F)F)nc32)cc1
16
16
[0.11904872 0.32421875 0.34602483 0.43671876]
[0.11525736 0.45625001 0.88465084 0.55234377]
1H NMR
600 MHz
DMSO-d6
9.24 (s, 1H), 8.65 (d, J = 8.2 Hz, 1H), 7.58 (d, J = 8.2 Hz, 1H), 7.38 (d, J = 2.6 Hz, 1H), 7.20 (d, J = 8.8 Hz, 2H), 7.02 (dd, J = 8.8, 2.6 Hz, 1H), 6.87 (d, J = 8.8 Hz, 2H), 6.79 (d, J = 8.8 Hz, 1H), 5.46 (s, 2H), 4.28-4.15 (m, 4H), 3.69 (s, 3H)
null
[('s', [], '1H', 9.24, 9.24), ('d', ['8.2Hz'], '1H', 8.65, 8.65), ('d', ['8.2Hz'], '1H', 7.58, 7.58), ('d', ['2.6Hz'], '1H', 7.38, 7.38), ('d', ['8.8Hz'], '2H', 7.2, 7.2), ('dd', ['8.8Hz', '2.6Hz'], '1H', 7.02, 7.02), ('d', ['8.8Hz'], '2H', 6.87, 6.87), ('d', ['8.8Hz'], '1H', 6.79, 6.79), ('s', [], '2H', 5.46, 5.46), (...
19
12
19
10.1021_acs.orglett.4c02707
COc1ccc(Cn2nc(Nc3ccc4c(c3)OCCO4)c3ccc(C(F)(F)F)nc32)cc1
16
16
[0.11904872 0.32421875 0.34602483 0.43671876]
[0.11525736 0.45625001 0.88465084 0.55234377]
19F NMR
565 MHz
DMSO-d6
-65.4
null
[(-65.4, None, None)]
3
1
1
10.1021_acs.orglett.4c02707
C(F)(F)(F)c1ccc2c(Nc3ccc4c(c3)OCCO4)nn(C3CCOCC3)c2n1
17
17
[0.11879597 0.13281251 0.33515626 0.25683596]
[0.11449909 0.27851563 0.88465084 0.39414065]
1H NMR
600 MHz
DMSO-d6
9.26 (s, 1H), 8.65 (d, J = 8.1 Hz, 1H), 7.58 (d, J = 8.2 Hz, 1H), 7.47 (d, J = 2.6 Hz, 1H), 7.04 (dd, J = 8.8, 2.6 Hz, 1H), 6.83 (d, J = 8.8 Hz, 1H), 5.01-4.86 (m, 1H), 4.35-4.13 (m, 4H), 4.07-3.96 (m, 2H), 3.60 (td, J = 11.8, 1.7 Hz, 2H), 2.21 (qd, J = 12.2, 4.6 Hz, 2H), 1.91-1.84 (m, 2H)
null
[('s', [], '1H', 9.26, 9.26), ('d', ['8.1Hz'], '1H', 8.65, 8.65), ('d', ['8.2Hz'], '1H', 7.58, 7.58), ('d', ['2.6Hz'], '1H', 7.47, 7.47), ('dd', ['8.8Hz', '2.6Hz'], '1H', 7.04, 7.04), ('d', ['8.8Hz'], '1H', 6.83, 6.83), ('m', [], '1H', 5.01, 4.86), ('m', [], '4H', 4.35, 4.13), ('m', [], '2H', 4.07, 3.96), ('td', ['11.8...
19
11
19
10.1021_acs.orglett.4c02707
C(F)(F)(F)c1ccc2c(Nc3ccc4c(c3)OCCO4)nn(C3CCOCC3)c2n1
17
17
[0.11879597 0.13281251 0.33515626 0.25683596]
[0.11449909 0.27851563 0.88465084 0.39414065]
19F NMR
565 MHz
DMSO-d6
-65.3
null
[(-65.3, None, None)]
3
1
1
10.1021_acs.orglett.4c02707
C=CCn1nc(Nc2ccc3c(c2)OCCO3)c2ccc(C(F)(F)F)nc21
17
17
[0.11879597 0.68281255 0.33515626 0.80156253]
[0.11424633 0.82031258 0.88465084 0.87656256]
1H NMR
600 MHz
DMSO-d6
9.24 (s, 1H), 8.65 (d, J = 8.2 Hz, 1H), 7.57 (d, J = 8.2 Hz, 1H), 7.40 (d, J = 2.6 Hz, 1H), 7.03 (dd, J = 8.8, 2.6 Hz, 1H), 6.80 (d, J = 8.8 Hz, 1H), 6.09-5.85 (m, 1H), 5.17 (dq, J = 10.4, 1.5 Hz, 1H), 5.06 (dq, J = 10.4, 1.5 Hz, 1H), 4.95 (dt, J = 5.3, 1.5 Hz, 2H), 4.25-4.11 (m, 4H)
null
[('s', [], '1H', 9.24, 9.24), ('d', ['8.2Hz'], '1H', 8.65, 8.65), ('d', ['8.2Hz'], '1H', 7.57, 7.57), ('d', ['2.6Hz'], '1H', 7.4, 7.4), ('dd', ['8.8Hz', '2.6Hz'], '1H', 7.03, 7.03), ('d', ['8.8Hz'], '1H', 6.8, 6.8), ('m', [], '1H', 6.09, 5.85), ('dq', ['10.4Hz', '1.5Hz'], '1H', 5.17, 5.17), ('dq', ['10.4Hz', '1.5Hz'], ...
15
11
15
10.1021_acs.orglett.4c02707
C=CCn1nc(Nc2ccc3c(c2)OCCO3)c2ccc(C(F)(F)F)nc21
17
17
[0.11879597 0.68281255 0.33515626 0.80156253]
[0.11424633 0.82031258 0.88465084 0.87656256]
19F NMR
565 MHz
DMSO-d6
-65.4
null
[(-65.4, None, None)]
3
1
1
10.1021_acs.orglett.4c02707
CN(N)c1nc(Cl)ccc1Br
19
19
[0.1185432 0.31562503 0.26185663 0.37734377]
[0.11576287 0.39648441 0.88212326 0.47226565]
1H NMR
400 MHz
DMSO-d6
7.88 (d, J = 8.0 Hz, 1H), 6.87 (d, J = 8.0 Hz, 1H), 4.61 (s, 2H), 3.02 (s, 3H)
null
[('d', ['8.0Hz'], '1H', 7.88, 7.88), ('d', ['8.0Hz'], '1H', 6.87, 6.87), ('s', [], '2H', 4.61, 4.61), ('s', [], '3H', 3.02, 3.02)]
7
4
7
10.1021_acs.orglett.4c02707
Cc1c(Br)cnc(N(C)N)c1Br
19
19
[0.1185432 0.62539068 0.26135112 0.69960939]
[0.11576287 0.7179688 0.88313423 0.79453131]
1H NMR
400 MHz
DMSO-d6
8.31 (s, 1H), 4.62 (s, 2H), 2.96 (s, 3H), 2.52 (s, 3H)
null
[('s', [], '1H', 8.31, 8.31), ('s', [], '2H', 4.62, 4.62), ('s', [], '3H', 2.96, 2.96), ('s', [], '3H', 2.52, 2.52)]
9
4
9
10.1021_acs.orglett.4c02707
Cc1nc(N(C)N)c(Br)cc1Cl
20
20
[0.11879597 0.11308594 0.26084561 0.17441407]
[0.11525736 0.19296875 0.88363977 0.36640626]
1H NMR
400 MHz
DMSO-d6
7.92 (s, 1H), 4.62 (s, 2H), 2.93 (s, 3H), 2.39 (s, 3H)
null
[('s', [], '1H', 7.92, 7.92), ('s', [], '2H', 4.62, 4.62), ('s', [], '3H', 2.93, 2.93), ('s', [], '3H', 2.39, 2.39)]
9
4
9
10.1021_acs.orglett.4c02707
Cc1nc(N(C)N)c(Br)cc1Cl
20
20
[0.11879597 0.11308594 0.26084561 0.17441407]
[0.11525736 0.19296875 0.88363977 0.36640626]
13C NMR
101 MHz
DMSO-d6
158.4, 150.7, 141.5, 121.9, 107.5, 44.0, 21.6
null
[(158.4, None, None), (150.7, None, None), (141.5, None, None), (121.9, None, None), (107.5, None, None), (44.0, None, None), (21.6, None, None)]
7
7
7
10.1021_acs.orglett.4c02707
COC(=O)c1cnc(N(C)N)c(Br)c1
20
20
[0.11778494 0.42460941 0.28612134 0.50507817]
[0.11576287 0.5226563 0.88313423 0.59921877]
1H NMR
400 MHz
DMSO-d6
8.61 (d, J = 2.0 Hz, 1H), 8.16 (d, J = 2.0 Hz, 1H), 5.40 (s, 2H), 3.81 (s, 3H), 3.20 (s, 3H)
null
[('d', ['2.0Hz'], '1H', 8.61, 8.61), ('d', ['2.0Hz'], '1H', 8.16, 8.16), ('s', [], '2H', 5.4, 5.4), ('s', [], '3H', 3.81, 3.81), ('s', [], '3H', 3.2, 3.2)]
10
5
10
10.1021_acs.orglett.4c02707
COC(=O)c1cnc(N(C)N)c(Br)c1
20
20
[0.11778494 0.42460941 0.28612134 0.50507817]
[0.11576287 0.5226563 0.88313423 0.59921877]
13C NMR
101 MHz
DMSO-d6
164.3, 161.0, 147.0, 142.8, 117.5, 105.5, 52.0, 43.2
null
[(164.3, None, None), (161.0, None, None), (147.0, None, None), (142.8, None, None), (117.5, None, None), (105.5, None, None), (52.0, None, None), (43.2, None, None)]
8
8
8
10.1021_acs.orglett.4c02707
Cc1cc(N(C)N)c(Br)cn1
21
21
[0.11727941 0.26328127 0.24315259 0.32421875]
[0.11525736 0.34375004 0.8826287 0.41953127]
1H NMR
400 MHz
CDCl3
8.40 (s, 1H), 7.01 (s, 1H), 3.89 (s, 2H), 3.13 (s, 3H), 2.46 (s, 3H)
null
[('s', [], '1H', 8.4, 8.4), ('s', [], '1H', 7.01, 7.01), ('s', [], '2H', 3.89, 3.89), ('s', [], '3H', 3.13, 3.13), ('s', [], '3H', 2.46, 2.46)]
10
5
10
10.1021_acs.orglett.4c02707
Cc1cc(N(C)N)c(Br)cn1
21
21
[0.11727941 0.26328127 0.24315259 0.32421875]
[0.11525736 0.34375004 0.8826287 0.41953127]
13C NMR
101 MHz
DMSO-d6
158.0, 157.1, 151.4, 113.5, 107.9, 46.3, 23.6
null
[(158.0, None, None), (157.1, None, None), (151.4, None, None), (113.5, None, None), (107.9, None, None), (46.3, None, None), (23.6, None, None)]
7
7
7
10.1021_acs.orglett.4c02707
CN(N)c1c(Cl)cncc1Br
21
21
[0.11980699 0.55234377 0.23102024 0.61796878]
[0.11525736 0.63828127 0.8826287 0.81328128]
1H NMR
400 MHz
DMSO-d6
8.52 (s, 1H), 8.41 (s, 1H), 4.65 (s, 2H), 3.05 (s, 3H)
null
[('s', [], '1H', 8.52, 8.52), ('s', [], '1H', 8.41, 8.41), ('s', [], '2H', 4.65, 4.65), ('s', [], '3H', 3.05, 3.05)]
7
4
7
10.1021_acs.orglett.4c02707
CN(N)c1c(Cl)cncc1Br
21
21
[0.11980699 0.55234377 0.23102024 0.61796878]
[0.11525736 0.63828127 0.8826287 0.81328128]
13C NMR
101 MHz
DMSO-d6
153.8, 151.2, 149.5, 127.7, 118.0, 46.0
null
[(153.8, None, None), (151.2, None, None), (149.5, None, None), (127.7, None, None), (118.0, None, None), (46.0, None, None)]
6
6
6
10.1021_acs.orglett.4c02707
CN(N)c1ccc(Br)nc1Br
22
22
[0.11930148 0.11171876 0.26160389 0.17421877]
[0.11525736 0.19316407 0.8826287 0.24863284]
1H NMR
400 MHz
DMSO-d6
7.74 (d, J = 8.4 Hz, 1H), 7.60 (d, J = 8.4 Hz, 1H), 4.57 (s, 2H), 2.94 (s, 3H)
null
[('d', ['8.4Hz'], '1H', 7.74, 7.74), ('d', ['8.4Hz'], '1H', 7.6, 7.6), ('s', [], '2H', 4.57, 4.57), ('s', [], '3H', 2.94, 2.94)]
7
4
7
10.1021_acs.orglett.4c02707
CN(N)c1ccc(Br)nc1Br
22
22
[0.11930148 0.11171876 0.26160389 0.17421877]
[0.11525736 0.19316407 0.8826287 0.24863284]
13C NMR
101 MHz
DMSO-d6
150.1, 134.4, 131.9, 130.5, 127.3, 47.5
null
[(150.1, None, None), (134.4, None, None), (131.9, None, None), (130.5, None, None), (127.3, None, None), (47.5, None, None)]
6
6
6
10.1021_acs.orglett.4c02707
CN(N)c1cc(Cl)cnc1Br
22
22
[0.1185432 0.40234379 0.25857078 0.46328127]
[0.11475184 0.48203127 0.88212326 0.5382813 ]
1H NMR
400 MHz
DMSO-d6
8.05 (d, J = 2.4 Hz, 1H), 7.86 (d, J = 2.4 Hz, 1H), 4.61 (s, 2H), 2.97 (s, 3H)
null
[('d', ['2.4Hz'], '1H', 8.05, 8.05), ('d', ['2.4Hz'], '1H', 7.86, 7.86), ('s', [], '2H', 4.61, 4.61), ('s', [], '3H', 2.97, 2.97)]
7
4
7
10.1021_acs.orglett.4c02707
CN(N)c1cc(Cl)cnc1Br
22
22
[0.1185432 0.40234379 0.25857078 0.46328127]
[0.11475184 0.48203127 0.88212326 0.5382813 ]
13C NMR
101 MHz
DMSO-d6
150.9, 140.8, 133.7, 130.5, 128.5, 47.4
null
[(150.9, None, None), (140.8, None, None), (133.7, None, None), (130.5, None, None), (128.5, None, None), (47.4, None, None)]
6
6
6
10.1021_acs.orglett.4c02707
Cc1ncnc(N(C)N)c1Br
22
22
[0.11955423 0.69257817 0.23051473 0.76679692]
[0.11551012 0.78554689 0.88363977 0.86093756]
1H NMR
400 MHz
DMSO-d6
8.34 (s, 1H), 4.89 (s, 2H), 3.19 (s, 3H), 2.46 (s, 3H)
null
[('s', [], '1H', 8.34, 8.34), ('s', [], '2H', 4.89, 4.89), ('s', [], '3H', 3.19, 3.19), ('s', [], '3H', 2.46, 2.46)]
9
4
9
10.1021_acs.orglett.4c02707
Cc1ncnc(N(C)N)c1Br
22
22
[0.11955423 0.69257817 0.23051473 0.76679692]
[0.11551012 0.78554689 0.88363977 0.86093756]
13C NMR
101 MHz
DMSO-d6
165.0, 162.5, 154.0, 104.8, 42.8, 25.2
null
[(165.0, None, None), (162.5, None, None), (154.0, None, None), (104.8, None, None), (42.8, None, None), (25.2, None, None)]
6
6
6
10.1021_acs.orglett.4c02707
CSc1ncc2cc(Br)c(N(C)N)nc2n1
23
23
[0.11778494 0.17773439 0.30785849 0.23984377]
[0.11525736 0.25839846 0.88465084 0.33339845]
1H NMR
400 MHz
DMSO-d6
8.96 (s, 1H), 8.45 (s, 1H), 5.11 (s, 2H), 3.34 (s, 3H), 2.56 (s, 3H)
null
[('s', [], '1H', 8.96, 8.96), ('s', [], '1H', 8.45, 8.45), ('s', [], '2H', 5.11, 5.11), ('s', [], '3H', 3.34, 3.34), ('s', [], '3H', 2.56, 2.56)]
10
5
10
10.1021_acs.orglett.4c02707
CSc1ncc2cc(Br)c(N(C)N)nc2n1
23
23
[0.11778494 0.17773439 0.30785849 0.23984377]
[0.11525736 0.25839846 0.88465084 0.33339845]
13C NMR
101 MHz
DMSO-d6
171.9, 161.1, 158.2, 156.4, 142.3, 113.3, 106.3, 43.3, 13.8
null
[(171.9, None, None), (161.1, None, None), (158.2, None, None), (156.4, None, None), (142.3, None, None), (113.3, None, None), (106.3, None, None), (43.3, None, None), (13.8, None, None)]
9
9
9
10.1021_acs.orglett.4c02707
COc1ccc(CN(N)c2nc(C(F)(F)F)ccc2Br)cc1
23
24
[0.1185432 0.75781258 0.33035388 0.86093756]
[0.11525736 0.09394532 0.88363977 0.1890625 ]
1H NMR
600 MHz
CDCl3
7.96 (app dd, J = 7.9, 0.6 Hz, 1H), 7.35 (d, J = 8.7 Hz, 2H), 7.14 (d, J = 7.9 Hz, 1H), 6.89 (d, J = 8.7 Hz, 2H), 4.57 (s, 2H), 4.09-3.96 (m, 2H), 3.81 (s, 3H)
null
[('app dd', ['7.9Hz', '0.6Hz'], '1H', 7.96, 7.96), ('d', ['8.7Hz'], '2H', 7.35, 7.35), ('d', ['7.9Hz'], '1H', 7.14, 7.14), ('d', ['8.7Hz'], '2H', 6.89, 6.89), ('s', [], '2H', 4.57, 4.57), ('m', [], '2H', 4.09, 3.96), ('s', [], '3H', 3.81, 3.81)]
13
7
13
10.1021_acs.orglett.4c02707
COc1ccc(CN(N)c2nc(C(F)(F)F)ccc2Br)cc1
23
24
[0.1185432 0.75781258 0.33035388 0.86093756]
[0.11525736 0.09394532 0.88363977 0.1890625 ]
19F NMR
565 MHz
CDCl3
-68.1
null
[(-68.1, None, None)]
3
1
1
10.1021_acs.orglett.4c02707
C(F)(F)(F)c1ccc(Br)c(N(N)C2CCOCC2)n1
24
24
[0.11879597 0.39589845 0.27019763 0.49609379]
[0.11475184 0.51796877 0.8841453 0.61406253]
1H NMR
600 MHz
CDCl3
7.94 (dd, J = 7.9, 0.6 Hz, 1H), 7.13 (d, J = 7.9 Hz, 1H), 4.07-4.00 (m, 3H), 3.84 (tt, J = 11.4, 4.0 Hz, 1H), 3.46-3.36 (m, 2H), 2.22-2.08 (m, 2H), 1.61 (m, 2H)
null
[('dd', ['7.9Hz', '0.6Hz'], '1H', 7.94, 7.94), ('d', ['7.9Hz'], '1H', 7.13, 7.13), ('m', [], '3H', 4.07, 4.0), ('tt', ['11.4Hz', '4.0Hz'], '1H', 3.84, 3.84), ('m', [], '2H', 3.46, 3.36), ('m', [], '2H', 2.22, 2.08), ('m', [], '2H', 1.61, 1.61)]
13
6
12
10.1021_acs.orglett.4c02707
C(F)(F)(F)c1ccc(Br)c(N(N)C2CCOCC2)n1
24
24
[0.11879597 0.39589845 0.27019763 0.49609379]
[0.11475184 0.51796877 0.8841453 0.61406253]
19F NMR
565 MHz
CDCl3
-68.2
null
[(-68.2, None, None)]
3
1
1
10.1021_acs.orglett.4c02707
C=CCN(N)c1nc(C(F)(F)F)ccc1Br
24
25
[0.11904872 0.82031258 0.26969212 0.90781256]
[0.11525736 0.09379883 0.88363977 0.1890625 ]
1H NMR
600 MHz
CDCl3
7.93 (app dd, J = 7.8, 0.7 Hz, 1H), 7.12 (d, J = 7.8 Hz, 1H), 6.08-5.96 (m, 1H), 5.38-5.25 (m, 2H), 4.25-4.09 (br s, 2H), 4.07 (dt, J = 6.1, 1.3 Hz, 2H)
null
[('app dd', ['7.8Hz', '0.7Hz'], '1H', 7.93, 7.93), ('d', ['7.8Hz'], '1H', 7.12, 7.12), ('m', [], '1H', 6.08, 5.96), ('m', [], '2H', 5.38, 5.25), ('brs', [], '2H', 4.25, 4.09), ('dt', ['6.1Hz', '1.3Hz'], '2H', 4.07, 4.07)]
9
6
9
10.1021_acs.orglett.4c02707
C=CCN(N)c1nc(C(F)(F)F)ccc1Br
24
25
[0.11904872 0.82031258 0.26969212 0.90781256]
[0.11525736 0.09379883 0.88363977 0.1890625 ]
19F NMR
565 MHz
CDCl3
-68.2
null
[(-68.2, None, None)]
3
1
1
10.1002_adsc.202300487
CC(C)(C)C(=O)n1ccc2ccccc21
2
2
[0.14484579 0.20019533 0.23570235 0.26816408]
[0.14084148 0.28984376 0.85885684 0.45390628]
1H NMR
600 MHz
CDCl3
8.54 (d, J = 7.8 Hz, 1H), 7.74 (d, J = 3.7 Hz, 1H), 7.57 (d, J = 7.8 Hz, 1H), 7.36 (t, J = 7.8 Hz, 1H), 7.28 (t, J = 7.8 Hz, 1H), 6.63 (d, J = 3.7 Hz, 1H), 1.53 (s, 9H), 13
null
[('d', ['7.8Hz'], '1H', 8.54, 8.54), ('d', ['3.7Hz'], '1H', 7.74, 7.74), ('d', ['7.8Hz'], '1H', 7.57, 7.57), ('t', ['7.8Hz'], '1H', 7.36, 7.36), ('t', ['7.8Hz'], '1H', 7.28, 7.28), ('d', ['3.7Hz'], '1H', 6.63, 6.63), ('s', [], '9H', 1.53, 1.53)]
15
7
15