tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate → HCID 49839495, compound

HRID 472563Notes

Reaction equation

HRID 472563 reaction equation
Cl[C:2]1[N:18]=[C:5]2[C:6]([C:10]3[CH:15]=[N:14][C:13]([O:16][CH3:17])=[CH:12][N: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].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[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]=[N:14][C:13]([O:16][CH3:17])=[CH:12][N: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

4

Reactant 3

HCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylateHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67481435HCID 67481435, compound

Product 1

HCID 49839495HCID 49839495, compound

Procedure

4-{4-[8-(5-Methoxy-pyrazin-2-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-(5-methoxy-pyrazin-2-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 (0.039 g, 19%). MP=193-195° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.75 (s, 1H), 9.69 (s, 1H), 8.87 (d, 1H), 8.49 (m, 1H), 8.35 (m, 1H), 7.65 (m, 2H), 7.20 (m, 3H), 4.08 (m, 2H), 4.02 (s, 3H), 2.80 (m, 2H), 2.62 (m, 1H), 1.72 (m, 2H), 1.51 (m, 2H), 1.40 (s, 9H). MS=502 (MH)+.

Sources & evidence

ORD record
ord-cb9a9bed7c03435d8bd00b7b91b0c372
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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