tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate → HCID 49839726, compound

HRID 1890076Notes

Reaction equation

HRID 1890076 reaction equation
Cl[C:2]1[N:19]=[C:5]2[C:6]([C:10]3[CH:11]=[C:12]([N:16]([CH3:18])[CH3:17])[CH:13]=[CH:14][CH:15]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([C:33]2[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([C:33]2[CH:38]=[CH:37][C:36]([NH:39][C:2]3[N:19]=[C:5]4[C:6]([C:10]5[CH:15]=[CH:14][CH:13]=[C:12]([N:16]([CH3:18])[CH3:17])[CH:11]=5)=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)=[CH:35][CH:34]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

3

Reactant 2

HCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylateHCID 67481465HCID 67481465, compound

Product 1

HCID 49839726HCID 49839726, compound

Procedure

4-{4-[8-(3-Dimethylamino-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester was prepared from [3-(2-chloro-[1,2,4]-triazolo[1,5-a]pyridin-8-yl)-phenyl]-dimethyl-amine (0.250 g, 0.917 mmol) and 4-(4-amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.304 g, 1.10 mmol) in a manner analogous to Example 311a and 311b to give product (0.288 g, 61%). MP=95-98° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.57 (s, 1H), 8.74 (d, 1H), 7.82 (d, 1H), 7.62 (d, 2H), 7.50 (s, 1H) 7.32 (m, 2H), 7.15 (m, 3H), 6.80 (d, 1H), 4.05 (m, 2H), 3.00 (s, 6H), 2.80 (br m, 2H), 2.60 (m, 1H), 1.75 (m, 2H), 1.45 (m, 2H), 1.41 (s, 9H). MS=513 (MH)+.

Sources & evidence

ORD record
ord-6223ff5284e74923b9637f2472038cd3
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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