tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate → HCID 59612611, compound

HRID 1890056Notes

Reaction equation

HRID 1890056 reaction equation
Cl[C:2]1[N:21]=[C:5]2[C:6]([C:10]3[CH:15]=[CH:14][C:13]([CH:16]([F:18])[F:17])=[CH:12][C:11]=3[O:19][CH3:20])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([C:35]2[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=2)[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([C:35]2[CH:40]=[CH:39][C:38]([NH:41][C:2]3[N:21]=[C:5]4[C:6]([C:10]5[CH:15]=[CH:14][C:13]([CH:16]([F:18])[F:17])=[CH:12][C:11]=5[O:19][CH3:20])=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)=[CH:37][CH:36]=2)[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

3

Reactant 2

HCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylateHCID 67481566HCID 67481566, compound

Product 1

HCID 59612611HCID 59612611, compound

Procedure

4-{4-[8-(4-Difluoromethyl-2-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester was prepared from 2-chloro-8-(4-difluoromethyl-2-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridine (0.150 g, 0.484 mmol) and 4-(4-amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.161 g, 0.581 mmol) in a manner analogous to Example 311a and 311b to give product (0.191 g, 72%). MP=95-100° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.57 (s, 1H), 8.78 (d, 1H), 7.70 (d, 1H), 7.55 (m, 3H), 7.32 (s, 1H), 7.25 (m, 1H), 7.15 (d, 2H), 7.10 (br m, 1H), 7.05 (m, 1H), 4.10 (m, 2H), 3.78 (s, 3H), 2.78 (br m, 2H), 2.55 (m, 1H), 1.75 (m, 2H), 1.45 (m, 2H), 1.41 (s, 9H): MS=550 (MH)+.

Sources & evidence

ORD record
ord-6d732c24031a4aea8c9c5f16e9df8771
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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