tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate → HCID 49839252, compound

HRID 1890029Notes

Reaction equation

HRID 1890029 reaction equation
BrC1C2N(N=C(Cl)N=2)C=CC=1.COC1(B(O)O)C=CC(C(F)(F)F)=CN1.[Cl:27][C:28]1[N:48]=[C:31]2[C:32]([C:36]3[C:37]([O:46][CH3:47])=[N:38][CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=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[C:37]([O:46][CH3:47])=[N:38][CH:39]=[C:40]([C:42]([F:44])([F:45])[F:43])[CH:41]=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[C:37]([O:46][CH3:47])=[N:38][CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=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 67478796HCID 67478796, compoundHCID 674813708-Bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridineHCID 67481456HCID 67481456, compound

Product 2

HCID 49839252HCID 49839252, compoundHCID 67481456HCID 67481456, compound

Procedure

2-Chloro-8-(2-methoxy-5-trifluoromethyl-pyridin-3-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 2-methoxy-5-trifluoromethylpyridineboronic acid in a manner analogous to Example 2c (0.46 g, 65%). MP=183-185° C. MS=329 (MH)+. 277b) [4-{4-[8-(2-Methoxy-5-trifluoromethyl-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester was prepared from 2-chloro-8-(2-methoxy-5-trifluoromethyl-pyridin-3-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 (0.233 g, 41%). MP=142-144° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.75 (s, 1H), 8.80 (d, 1H), 8.65 (s, 1H), 8.55 (s, 1H), 7.85 (d, 1H), 7.55 (d, 2H), 7.02 (m, 3H), 4.05 (m, 2H), 3.90 (s, 3H), 2.6-2.8 (m, 3H), 1.65 (m, 2H), 1.40 (m, 11H). MS=569 (MH)+.

Sources & evidence

ORD record
ord-f2f7bbf40f494276999f9329e03367c8
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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