4-Methyl-piperazine-1-carboxylic acid methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amide → 4-Methyl-piperazine-1-carboxylic acid (4-amino-3-piperidin-1-yl-phenyl)-methyl-amide
Reaction equation
[CH3:1][N:2]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:13]=1)[C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]1)=[O:4]>CO.[Pd]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([N:2]([CH3:1])[C:3]([N:5]2[CH2:6][CH2:7][N:8]([CH3:11])[CH2:9][CH2:10]2)=[O:4])=[CH:13][C:14]=1[N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1Participants
Procedure
Using a procedure similar to Example 23, step (a), 4-methyl-piperazine-1-carboxylic acid methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amide (110 mg, 0.3 mmol, as prepared in the previous step) was stirred in MeOH in the presence of 5% Pd—C (65 mg) to afford crude 4-methyl-piperazine-1-carboxylic acid (4-amino-3-piperidin-1-yl-phenyl)-methyl-amide as an oil, which in a manner similar to Example 4, step (c) was coupled to 5-cyano-furan-2-carbonyl chloride (64.6 μL, 412 mmol) in the presence of DIEA (115 μL, 0.6 mmol) using a procedure similar to Example 2 to afford 54.4 mg (40%) of the title compound as a bright yellow solid. 1H-NMR (CDCl3, 400 MHz): δ 9.62 (s, 1H), 8.41 (d, 1H, J=8.5 Hz), 7.29 (d, 1H, J=3.8 Hz), 7.24 (d, 1H, J=3.8 Hz), 6.95-6.92 (m, 2H), 3.24-3.26 (M, 4H), 3.22 (s, 3H), 2.84-2.82 (m, 4H), 2.21-2.26 (m, 7H), 1.84-1.79 (m, 4H), 1.66 (m, 2H); Mass spectrum (ESI, m/z): Calcd. for C24H30N6O3, 451.2 (M+H), found 451.1.
Workup
- customas prepared in the previous step)
Sources & evidence
- ORD record
- ord-fe77e349b839422cb757b73feebc614f
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07705042B2
Reaction notes
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