tert-Butyl 4-(3-aminophenyl)piperidine-1-carboxylate → 4-{3-[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 472467Notes

Reaction equation

HRID 472467 reaction equation
Cl[C:2]1[N:20]=[C:5]2[C:6]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][CH:31]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([NH2:40])[CH:35]=2)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][CH:31]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([NH:40][C:2]3[N:20]=[C:5]4[C:6]([C:10]5[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=5)=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)[CH:35]=2)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 3

HCID 22049268tert-Butyl 4-(3-aminophenyl)piperidine-1-carboxylateHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 674814372-Chloro-8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 498386484-{3-[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester

Procedure

180 c) 4-{3-[8-(4-Methanesulfonyl-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-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine (500.0 mg, 1.625 mmol) and 4-(3-amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (500.0 mg, 1.809 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (90.0 mg, 0.165 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a yellow foam (0.59 g, 66%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.52 (d, J=6.6 Hz, 1H), 8.23 (d, J=8.4 Hz, 2H), 8.09 (d, J=8.4 Hz, 2H), 7.66 (d, J=7.4 Hz, 1H), 7.47-7.41 (m, 2H), 7.30 (t, J=7.6 Hz, 1H), 7.03 (t, J=7.0 Hz, 1H), 6.92-6.85 (m, 2H), 4.27 (br m, 2H), 3.10 (s, 3H), 2.83 (t, J=11.9 Hz, 2H), 2.73-2.63 (m, 1H), 1.84 (d, J=13.1 Hz, 2H), 1.73-1.60 (m, 2H), 1.49 (s, 9H). MS=538 (MH)+.

Sources & evidence

ORD record
ord-e191cf66d3de42a484429679d6433571
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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