2-Ethyl butylamine → 2-[(1-Adamantylmethyl)amino]nicotinic acid

HRID 601109Notes

Reaction equation

HRID 601109 reaction equation
Cl[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[C:13]12([CH2:23][NH2:24])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2.C(C(CC)CN)C>>[C:13]12([CH2:23][NH:24][C:2]3[N:12]=[CH:11][CH:10]=[CH:9][C:3]=3[C:4]([OH:6])=[O:5])[CH2:20][CH:19]3[CH2:18][CH:17]([CH2:16][CH:15]([CH2:21]3)[CH2:14]1)[CH2:22]2

Participants

4

Reactant 3

HCID 120492-Ethyl butylamineHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 2796614Ethyl chloronicotinate

Product 1

HCID 670640232-[(1-Adamantylmethyl)amino]nicotinic acid

Procedure

The title compound was prepared according to the procedure of Example 3A substituting 2-chloronicotinic acid for ethyl 2-chloronicotinate and 1-adamantanemethylamine for 2-ethylbutylamine (0.185 g, 79%). MS (ESI+) m/z 287.1 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 1.74 (m, 12H), 2.00 (s, 3H), 3.31 (m, 2H), 6.60 (dd, J=7.35, 5.52 Hz, 1H), 7.96 (dd, J=5.33, 2.02 Hz, 1H), 8.26 (dd, J=7.35, 1.84 Hz, 1H).

Sources & evidence

ORD record
ord-20191904d9cf426497a6bdf127ca05a9
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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