Trifluoroacetic acid → 5-(3-(ethylthio)phenyl)-3-methyl-8-((1-methylpiperidin-4-yl)methoxy)-9H-pyrido[2,3-b]indole
Reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)=[C:17]3[C:13]=2[C:14]2[CH:33]=[C:32]([CH3:34])[CH:31]=[N:30][C:15]=2[NH:16]3)[CH:9]=[CH:10][CH:11]=1)(=O)=O)[CH3:2].C(O)(C(F)(F)F)=O>>[CH2:1]([S:3][C:6]1[CH:7]=[C:8]([C:12]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]3[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]3)=[C:17]3[C:13]=2[C:14]2[CH:33]=[C:32]([CH3:34])[CH:31]=[N:30][C:15]=2[NH:16]3)[CH:9]=[CH:10][CH:11]=1)[CH3:2]Participants
3
Procedure
The title compound was synthesized using an analogous procedure to that outlined in the preparation of Compound 176. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.28 (t, J=7.20 Hz, 3 H) 1.48-1.56 (m, 2 H) 2.09-2.20 (m, 1 H) 2.25 (br. s., 2 H) 2.27 (s, 3 H) 2.80 (d, J=4.55 Hz, 3 H) 3.03 (q, J=7.16 Hz, 4 H) 3.53 (d, J=11.37 Hz, 2 H) 4.08 (d, J=6.82 Hz, 2 H) 7.00 (d, J=8.08 Hz, 1 H) 7.10 (d, J=8.34 Hz, 1 H) 7.36-7.52 (m, 4 H) 7.59 (s, 1 H) 8.27 (s, 1 H) 9.41 (br. s., 1 H) 11.95 (s, 1 H); [M+H] calc'd for C27H32N3OS, 446.2; found, 446.4; [M+H+TFA] calc'd for C29H33N3O3F3S, 560.2; found, 560.4.
Sources & evidence
- ORD record
- ord-457b6c68256e4b2da570d009158ac98f
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119655B2
Reaction notes
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