Triethylamine → 2-Phenoxy-N-[3-(4-piperidinyl) phenyl]nicotinamide

HRID 1452652

反応式

HRID 1452652 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[O:21]([C:28]1[N:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>>[O:21]([C:28]1[N:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[CH:3]=1)=[O:31])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1.[O:21]([C:28]1[C:29]([C:30]([NH:1][C:2]2[CH:3]=[C:4]([CH:8]3[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]3)[CH:5]=[CH:6][CH:7]=2)=[O:31])=[CH:33][CH:34]=[CH:35][N:36]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27743062-Phenoxypyridine-3-carbonyl chlorideHCID 22049268tert-Butyl 4-(3-aminophenyl)piperidine-1-carboxylate

生成物 2

HCID 575269302-Phenoxy-N-[3-(4-piperidinyl) phenyl]nicotinamideHCID 68867278Tert-butyl 4-(3-{[(2-phenoxy-3-pyridinyl)carbonyl]amino}phenyl)-1-piperidinecarboxylate

実験手順

A mixture of tert-butyl 4-[3-(amino)phenyl]-1-piperidinecarboxylate (0.15 mmol), 2-phenoxynicotinoyl chloride (0.23 mmol) and triethylamine (0.30 mmol) in 3 mL of solvent (CH2Cl2:THF, 1:3) was stirred at room temperature for 12 hours. The reaction mixture was purified by preparative TLC (silica, EtOAc:hexane 1:1) to afford the desired product, tert-butyl 4-(3-{[(2-phenoxy-3-pyridinyl)carbonyl]amino}phenyl)-1-piperidinecarboxylate. Trifluoroacetic acid (1.0 mL) was added to the purified product dissolved in 1.0 mL of CH2Cl2 and the solution was stirred at room temperature for 1 minute. The reaction mixture was concentrated in vacuo to afford the TFA salt of the desired product. 1H NMR (400 MHz, CDCl3) δ 9.85 (s, 1H), 8.76-8.64 (br, 1H), 8.30-8.14 (br, 1H), 7.67 (s, 1H), 7.49 (t, 2H, J=7.8 Hz), 7.42-7.29 (m, 3H), 7.24 (t, 3H, J=5.2 Hz), 7.03 (d, 1H, J=7.2 Hz), 3.59 (bd, 2H, J=11.5), 3.16-3.02 (m, 2H), 2.9-2.79 (m, 1H), 2.14-2.01 (m, 4H); ESIMS m/e: 374.1 [M+H]+.

後処理

  1. customThe reaction mixture was purified by preparative TLC (silica, EtOAc:hexane 1:1)

出典と根拠

ORDレコード
ord-2d67ed583eeb4638b5ac5ba9380981ae
出典データセット
uspto-grants-2009_01
特許番号
US07473698B2

関連ノート

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