tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate → 4-{4-[8-(1-(4-Fluoro-phenyl)-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1890030Notes

Reaction equation

HRID 1890030 reaction equation
Br[C:2]1[C:3]2[N:4]([N:8]=[C:9](Cl)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]=[C:22](B(O)O)[CH:21]=[N:20]2)=[CH:15][CH:14]=1.[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH:38]=[C:37]([C:39]3[N:47]=[C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][N:41]4[N:40]=3)[CH:36]=[N:35]2)=[CH:30][CH:29]=1.[C:48]([O:52][C:53]([N:55]1[CH2:60][CH2:59][CH:58]([C:61]2[CH:66]=[CH:65][C:64]([NH2:67])=[CH:63][CH:62]=2)[CH2:57][CH2:56]1)=[O:54])([CH3:51])([CH3:50])[CH3:49].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH:38]=[C:37]([C:39]3[N:47]=[C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][N:41]4[N:40]=3)[CH:36]=[N:35]2)=[CH:30][CH:29]=1.[C:48]([O:52][C:53]([N:55]1[CH2:60][CH2:59][CH:58]([C:61]2[CH:66]=[CH:65][C:64]([NH:67][C:9]3[N:10]=[C:3]4[C:2]([C:22]5[CH:21]=[N:20][N:19]([C:16]6[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=6)[CH:23]=5)=[CH:7][CH:6]=[CH:5][N:4]4[N:8]=3)=[CH:63][CH:62]=2)[CH2:57][CH2:56]1)=[O:54])([CH3:51])([CH3:49])[CH3:50]

Participants

7

Reactant 5

HCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylateHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 467386841-(4-Fluorophenyl)pyrazole-4-boronic acidHCID 674813708-Bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridineHCID 86648363[1-(4-fluoro-phenyl)1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyridine

Product 2

HCID 498394924-{4-[8-(1-(4-Fluoro-phenyl)-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl esterHCID 86648363[1-(4-fluoro-phenyl)1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyridine

Procedure

2-Chloro-8-([1-(4-fluoro-phenyl)1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyridine was prepared from 8-bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine and 1-(4-fluorophenyl)pyrazole-4-boronic acid in a manner analogous to Example 2c (0.45 g, 67%). 280b) 4-{4-[8-(1-(4-Fluoro-phenyl)-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester was prepared from 2-chloro-8-([1-(4-fluoro-phenyl)1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyridine and 4-(4-amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester with 2,2′-bis-dicyclohexylphosphanyl-biphenyl as the ligand in a manner analogous to Example 2d (0.077 g, 23%). MP=176-178° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.62 (s, 1H), 9.26 (s, 1H), 8.76 (m, 2H), 7.95 (m, 3H), 7.65 (m, 2H), 7.45 (m, 2H), 7.15 (m, 2H), 7.09 (m, 1H), 4.08 (m, 2H), 2.80 (m, 2H), 2.63 (m, 1H), 1.73 (m, 2H), 1.48 (m, 2H), 1.42 (s, 9H). MS=554 (MH)+.

Sources & evidence

ORD record
ord-5738c2222f8448c38c65a12d5a6933a8
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

Loading…