5-Methoxy-1,3-dimethyl-1H-pyrazole-4-carbaldehyde → N-(2-Aminophenyl)-4-{1-[(5-methoxy-1,3-dimethyl-1H-pyrazol-4-yl)methyl]piperidin-4-yl}benzamide

HRID 222400Notes

Reaction equation

HRID 222400 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][O:31][C:32]1[N:36]([CH3:37])[N:35]=[C:34]([CH3:38])[C:33]=1[CH:39]=O>>[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:28]=[CH:29][C:7]([CH:4]2[CH2:3][CH2:2][N:1]([CH2:39][C:33]3[C:34]([CH3:38])=[N:35][N:36]([CH3:37])[C:32]=3[O:31][CH3:30])[CH2:6][CH2:5]2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 27643045-Methoxy-1,3-dimethyl-1H-pyrazole-4-carbaldehydeHCID 59830875Tert-butyl 2-[(4-piperidin-4-ylbenzoyl)amino]phenylcarbamate

Product 1

HCID 16049851N-(2-Aminophenyl)-4-{1-[(5-methoxy-1,3-dimethyl-1H-pyrazol-4-yl)methyl]piperidin-4-yl}benzamideYield 36%

Procedure

Using an analogous procedure to that described in Example 3, tert-butyl 2-[(4-piperidin-4-ylbenzoyl)amino]phenylcarbamate (prepared as described in Method 1 below; 200 mg, 0.51 mmol) was reacted with 5-methoxy-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (92.6 mg, 0.60 mmol) to give the title compound (68 mg, 36%); NMR Spectrum: (DMSO d6) δ 1.63 (m, 2H), 1.78 (m, 2H), 2.00 (m, 2H), 2.06 (s, 3H), 2.57 (m, 1H), 2.94 (m, 2H), 3.25 (s, 2H), 3.50 (s, 3H), 3.99 (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+434.

Sources & evidence

ORD record
ord-377120f0c10946299f7d50a0a7c8220a
Source dataset
uspto-grants-2012_06
Patent number
US08207202B2

Reaction notes

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