1,3,5-trimethyl-1H-pyrazole-4-carboxaldehyde → N-(2-Aminophenyl)-4-{1-[(1,3,5-trimethyl-1H-pyrazol-4-yl)methyl]piperidin-4-yl}benzamide

HRID 222402Notes

Reaction equation

HRID 222402 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:29]=[CH:28][C:10]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH:20]C(=O)OC(C)(C)C)=[O:12])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[CH3:30][N:31]1[C:35]([CH3:36])=[C:34]([CH:37]=O)[C:33]([CH3:39])=[N:32]1>>[NH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:13][C:11](=[O:12])[C:10]1[CH:9]=[CH:8][C:7]([CH:4]2[CH2:5][CH2:6][N:1]([CH2:37][C:34]3[C:33]([CH3:39])=[N:32][N:31]([CH3:30])[C:35]=3[CH3:36])[CH2:2][CH2:3]2)=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 7365151,3,5-trimethyl-1H-pyrazole-4-carboxaldehydeHCID 59830875Tert-butyl 2-[(4-piperidin-4-ylbenzoyl)amino]phenylcarbamate

Product 1

HCID 16225379N-(2-Aminophenyl)-4-{1-[(1,3,5-trimethyl-1H-pyrazol-4-yl)methyl]piperidin-4-yl}benzamideYield 56%

Procedure

Using an analogous procedure to that described in Example 5, tert-butyl 2-[(4-piperidin-4-ylbenzoyl)amino]phenylcarbamate (prepared as described in Method 1 below; 200 mg, 0.51 mmol) was reacted with 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde (83.5 mg, 0.60 mmol) to give the title compound (70 mg, 56%); NMR Spectrum: (DMSO d6) δ 1.65 (m, 2H), 1.77 (m, 2H), 1.98 (m, 2H), 2.09 (s, 3H), 2.18 (s, 3H), 2.57 (m, 1H), 2.92 (m, 2H), 3.24 (s, 2H), 3.63 (s, 3H), 4.86 (br s, 2H), 6.60 (m, 1H), 6.78 (d, 1H), 6.97 (m, 1H), 7.17 (d, 1H), 7.37 (d, 2H), 7.91 (d, 2H), 9.55 (s, 1H); Mass Spectrum: M+H+418.

Sources & evidence

ORD record
ord-f894c24624ac4d06b3ab5a5f49e3429f
Source dataset
uspto-grants-2012_06
Patent number
US08207202B2

Reaction notes

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