1-Methylpiperazin-2-one → 6-chloro-1-methyl-2-[5-(4-methyl-3-oxo-piperazin-1-ylmethyl)-pyridin-3-yl]-1H-indole-3-carbonitrile
Reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]#[N:21])=[C:7]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH:18]=O)[CH:17]=3)[N:8]2[CH3:11])=[CH:4][CH:3]=1.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][C:24]1=[O:29]>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]#[N:21])=[C:7]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH2:18][N:26]4[CH2:27][CH2:28][N:23]([CH3:22])[C:24](=[O:29])[CH2:25]4)[CH:17]=3)[N:8]2[CH3:11])=[CH:4][CH:3]=1Participants
3
Procedure
6-Chloro-2-(5-formyl-pyridin-3-yl)-1-methyl-1H-indole-3-carbonitrile (Example 126) and 1-methyl-piperazin-2-one are processed according to the method described in Example 170 to give 6-chloro-1-methyl-2-[5-(4-methyl-3-oxo-piperazin-1-ylmethyl)-pyridin-3-yl]-1H-indole-3-carbonitrile. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.70 (br. s., 2H), 2.82 (s, 3H), 3.09 (s, 2H), 3.29 (dd, J=11.0, 5.4 Hz, 2H), 3.73 (s, 2H), 3.80 (s, 3H), 7.36 (dd, J=8.6, 1.8 Hz, 1H), 7.72 (d, J=8.3 Hz, 1H), 7.96 (d, J=1.5 Hz, 1H), 8.09 (s, 1H), 8.74 (d, J=2.0 Hz, 1H), 8.81 (d, J=2.0 Hz, 1H). HRMS (ESI) m/z 394.1437 [(M+H)+ Calcd for C21H21ClN5O: 394.1435].
Sources & evidence
- ORD record
- ord-6c02c1fe252a4378844a7a8b902e4b71
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030334B2
Reaction notes
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