N-(2-Aminoethyl)piperidine → HCID 69147010、化合物

反応式

[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([OH:15])=[O:14])[CH:5]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[N:3]=1.N[CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([O:15][CH2:36][CH2:37][N:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[O:14])[CH:5]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[N:3]=1

参加物

反応物 4

HCID 33944N-(2-Aminoethyl)piperidine

HCID 757711-Hydroxybenzotriazole

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

HCID 59769653HCID 59769653、化合物2 回

生成物 1

HCID 69147010HCID 69147010、化合物収率 58.1%

実験手順

To a cold (0° C.) mixture of 3-(2-amino-3-cyano-6-{2-[(4-methoxybenzyl)oxy]phenyl}-4-pyridinyl)benzoic acid (starting compound 5, 1.35 g, 3.00 mmol), N-(2-aminoethyl)piperidine (0.420 g, 3.30 mmol), and 1-hydroxybenzotriazole (0.490 g, 3.60 mmol) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.69 g, 3.60 mmol) with stirring. The mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and partitioned between ethyl acetate and water. The separated organic phase was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The obtained solid was triturated with ethyl ether and dried under reduced pressure to give 2-(1-piperidinyl)ethyl 3-(2-amino-3-cyano-6-{2-[(4-methoxybenzyl)oxy]phenyl}-4-pyridinyl)benzoate (0.98 g, yield 58%).