tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate → 4-{4-[8-(4-Cyano-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1890071Notes

Reaction equation

HRID 1890071 reaction equation
Cl[C:2]1[N:18]=[C:5]2[C:6]([C:10]3[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:2]3[N:18]=[C:5]4[C:6]([C:10]5[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=5)=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)=[CH:34][CH:33]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

3

Reactant 2

HCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylateHCID 67481529HCID 67481529, compound

Product 1

HCID 596124024-{4-[8-(4-Cyano-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester

Procedure

4-{4-[8-(4-Cyano-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-cyano-phenyl)-[1,2,4]-triazolo[1,5-a]pyridine (0.164 g, 0.644 mmol) and 4-(4-amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.214 g, 0.773 mmol) in a manner analogous to Example 311a and 311b to give product (0.181 g, 57%). MP=96-100° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.70 (s, 1H), 8.85 (d, 1H), 8.40 (d, 2H), 8.00 (m, 3H), 7.62 (d, 2H), 7.15 (m, 3H), 4.05 (m, 2H), 2.80 (br m, 2H), 2.60 (m, 1H), 1.75 (m, 2H), 1.45 (m, 2H), 1.41 (s, 9H). MS=495 (MH)+.

Sources & evidence

ORD record
ord-89506c98e0904130a787c61bf6f977c8
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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