4-(2-Aminoethyl)piperidine, 4-BOC protected → HCID 66818606, compound

HRID 1024694Notes

Reaction equation

HRID 1024694 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([O:17][CH:18]([CH3:20])[CH3:19])[N:16]=2)[C:11]([OH:13])=O)=[CH:5][CH:4]=1)#[N:2].[C:23]([O:27][C:28](=[O:38])[NH:29][CH2:30][CH2:31][CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)([CH3:26])([CH3:25])[CH3:24]>>[C:23]([O:27][C:28](=[O:38])[NH:29][CH2:30][CH2:31][CH:32]1[CH2:33][CH2:34][N:35]([C:11]([C:10]2[CH:14]=[C:15]([O:17][CH:18]([CH3:20])[CH3:19])[N:16]=[C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:22][CH:21]=3)[CH:9]=2)=[O:13])[CH2:36][CH2:37]1)([CH3:26])([CH3:24])[CH3:25]

Participants

3

Reactant 2

HCID 15018494-(2-Aminoethyl)piperidine, 4-BOC protectedHCID 66818785HCID 66818785, compound

Product 1

HCID 66818606HCID 66818606, compoundYield 35.2%

Procedure

2-(4-cyano phenoxy)-6-isopropoxy isonicotinic acid (0.20 g, 0.67 mmol) and (2-piperidin-4-yl-ethyl)-carbamic acid tert-butyl ester (0.16 g, 0.7 mmol) were coupled using the procedure of Example 5(c) to afford 0.12 g of the required product. 1H NMR (DMSO-d6): δ 1.12 (2H, m), 1.15 (6H, d), 1.4 (9H, s), 1.6 (2H, m), 1.75 (1H, m), 2.7 (1H, m), 2.98 (3H, m), 3.5 (1H, m), 4.45 (1H, m), 4.8 (1H, m), 6.48 (1H, s), 6.58 (1H, s), 6.8 (1H, brs), 7.38 (2H, d), 7.9 (2H, d).

Sources & evidence

ORD record
ord-bdd9fed7848f40d4a4e03fe08e531e0e
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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