tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate → HCID 49839608, compound

HRID 1890033Notes

Reaction equation

HRID 1890033 reaction equation
BrC1C2N(N=C(Cl)N=2)C=CC=1.C1(C)C=CC(N2C=C(B(O)O)C=N2)=CC=1.[Cl:27][C:28]1[N:48]=[C:31]2[C:32]([C:36]3[CH:37]=[N:38][N:39]([C:41]4[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=4)[CH:40]=3)=[CH:33][CH:34]=[CH:35][N:30]2[N:29]=1.[C:49]([O:53][C:54]([N:56]1[CH2:61][CH2:60][CH:59]([C:62]2[CH:67]=[CH:66][C:65]([NH2:68])=[CH:64][CH:63]=2)[CH2:58][CH2:57]1)=[O:55])([CH3:52])([CH3:51])[CH3:50].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[Cl:27][C:28]1[N:48]=[C:31]2[C:32]([C:36]3[CH:37]=[N:38][N:39]([C:41]4[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=4)[CH:40]=3)=[CH:33][CH:34]=[CH:35][N:30]2[N:29]=1.[C:49]([O:53][C:54]([N:56]1[CH2:61][CH2:60][CH:59]([C:62]2[CH:67]=[CH:66][C:65]([NH:68][C:28]3[N:48]=[C:31]4[C:32]([C:36]5[CH:37]=[N:38][N:39]([C:41]6[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=6)[CH:40]=5)=[CH:33][CH:34]=[CH:35][N:30]4[N:29]=3)=[CH:64][CH:63]=2)[CH2:58][CH2:57]1)=[O:55])([CH3:52])([CH3:50])[CH3:51]

Participants

7

Reactant 5

HCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylateHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 46738688[1-(4-Methylphenyl)-1H-pyrazol-4-yl]boronic acidHCID 67481369HCID 67481369, compoundHCID 674813708-Bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine

Product 2

HCID 49839608HCID 49839608, compoundHCID 67481369HCID 67481369, compound

Procedure

2-Chloro-8-(1-p-tolyl-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-p-tolyl-pyrazole-4-boronic acid in a manner analogous to Example 2c (0.40 g, 68%). 287b) 4-{4-[8-(1-p-Tolyl-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-p-tolyl-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 (0.265 g, 40%). MP=124-125° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.60 (s, 1H), 9.24 (s, 1H), 8.68 (d, 1H), 8.64 (s, 1H), 7.98 (m, 1H), 7.77 (m, 2H), 7.66 (m, 2H), 7.40 (m, 2H), 7.21 (m, 2H), 4.08 (m, 2H), 2.80 (m, 2H), 2.62 (m, 1H), 2.38 (s, 3H), 1.73 (m, 2H), 1.48 (m, 2H), 1.41 (s, 3H). MS=550 (MH)+.

Sources & evidence

ORD record
ord-eda7a88f44dd4603ac332f0987d823b1
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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