4-(2-Aminoethyl)piperidine, 4-BOC protected → HCID 66818838, compound

HRID 1024705Notes

Reaction equation

HRID 1024705 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][C:6]([O:7][C:8]2[C:16]([F:17])=[CH:15][C:11]([C:12]([OH:14])=O)=[C:10]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=3)[N:9]=2)=[CH:5][CH:4]=1)#[N:2].[C:32]([O:36][C:37](=[O:47])[NH:38][CH2:39][CH2:40][CH:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)([CH3:35])([CH3:34])[CH3:33]>>[C:32]([O:36][C:37](=[O:47])[NH:38][CH2:39][CH2:40][CH:41]1[CH2:42][CH2:43][N:44]([C:12]([C:11]2[C:10]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:27])[F:28])[CH:20]=3)=[N:9][C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:31][CH:30]=3)=[C:16]([F:17])[CH:15]=2)=[O:14])[CH2:45][CH2:46]1)([CH3:35])([CH3:33])[CH3:34]

Participants

3

Reactant 2

HCID 15018494-(2-Aminoethyl)piperidine, 4-BOC protectedHCID 66818330HCID 66818330, compound

Product 1

HCID 66818838HCID 66818838, compoundYield 57.1%

Procedure

6-(4-cyano phenoxy)-5-fluoro-2-(3-trifluoromethoxy phenoxy)nicotinic acid (1.3 g, 2.99 mmol) and (2-piperidin-4-yl-ethyl)-carbamic acid tert-butyl ester (0.684 g, 3.0 mmol) were coupled using the procedure of Example 5(c) to afford 1.1 g of the required product. 1HNMR (DMSO-d6): δ 1.2 (2H, m), 1.4 (9H, d), 1.5 (2H, m), 1.6 (2H, m), 2.2 (1H, m), 2.35 (1H, m), 3.0 (3H, m), 3.7 (1H, m), 4.45 (1H, m), 6.78 (1H, m), 7.18 (1H, m), 7.26 (2H, m), 7.32 (1H, s), 7.46 (1H, m), 7.76 (1H, m), 7.86 (1H, s), 8.1 (1H, m).

Sources & evidence

ORD record
ord-42dde48f318a43a898fb3e95869c75c1
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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