Trifluoroacetic acid → 5-(3-ethoxyphenyl)-3-methyl-8-((1-methylpiperidin-4-yl)methoxy)-9H-pyrido[2,3-b]indole
Reaction equation
C(S([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)C.[C:35](O)([C:37](F)(F)F)=[O:36]>>[CH2:35]([O:36][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)[CH3:37]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 1.35 (t, J=6.95 Hz, 3H) 1.44-1.56 (m, 2H) 2.10-2.18 (m, 1H) 2.25 (br. s., 5H) 2.80 (d, J=4.80 Hz, 3H) 2.97-3.07 (m, 2H) 3.52 (d, J=11.62 Hz, 2H) 4.06-4.09 (m, 4H) 6.98-7.14 (m, 5H) 7.44 (t, J=7.71 Hz, 1H) 7.64 (s, 1H) 8.25 (s, 1H) 9.28 (br. s., 1H) 11.87 (s, 1H); [M+H] calc'd for C27H32N3O2, 430.2; found, 430.5; [M+H+TFA] calc'd for C29H33N3O4F3, 544.2; found, 544.4.
Sources & evidence
- ORD record
- ord-31349f6438d6438387bde36f040f3ace
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318939B2
Reaction notes
Loading…