tert-Butyl (2S)-2-methylpiperazine-1-carboxylate → 1,1-Dimethylethyl (2S)-2-methyl-4-{[6-(methylamino)-3-pyridinyl]methyl}-1-piperazinecarboxylate
Reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=O)=[CH:5][CH:4]=1.[CH3:11][C@H:12]1[CH2:17][NH:16][CH2:15][CH2:14][N:13]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>>[CH3:11][C@H:12]1[CH2:17][N:16]([CH2:9][C:6]2[CH:7]=[N:8][C:3]([NH:2][CH3:1])=[CH:4][CH:5]=2)[CH2:15][CH2:14][N:13]1[C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19]Participants
3
Procedure
The title compound was prepared from 6-(methylamino)-3-pyridinecarbaldehyde (D95) and 1,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate using a method similar to that described for D81 in Description D81A. δH (CDCl3, 400 MHz) 7.97 (1H, d), 7.44 (1H, dd), 6.38 (1H, d), 4.51 (1H, m), 4.17 (1H, br.s), 3.79 (1H, d), 3.38 (1H, d), 3.26 (1H, d), 3.07 (1H, td), 2.92 (3H, d), 2.74 (1H, m), 2.57 (1H, m), 2.09 (1H, dd), 1.96 (1H, m), 1.45 (9H, s), 1.20 (3H, d). MS (ES+): 343.2 (MNa+), 265.2, no molecular ion (MH+) observed.
Sources & evidence
- ORD record
- ord-c0b593a6501f4636b1e6908dc8be7218
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700599B2
Reaction notes
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