8-Amino-5,6,7,8-tetrahydroquinoline → Pyridine-2-carboxylic acid 4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzylamide

HRID 2308286

反応式

HRID 2308286 の反応式
[NH2:1][CH:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([NH:20][CH2:21][C:22]1[CH:33]=[CH:32][C:25]([CH2:26]OS(C)(=O)=O)=[CH:24][CH:23]=1)=[O:19]>O>[N:10]1[C:11]2[CH:2]([NH:1][CH2:26][C:25]3[CH:24]=[CH:23][C:22]([CH2:21][NH:20][C:18]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=4)=[O:19])=[CH:33][CH:32]=3)[CH2:3][CH2:4][CH2:5][C:6]=2[CH:7]=[CH:8][CH:9]=1

参加物

4

反応物 2

HCID 113555648-Amino-5,6,7,8-tetrahydroquinolineHCID 46205162Methanesulfonic acid 4-{[(pyridine-2-carbonyl)-amino]-methyl}-benzyl ester

生成物 1

HCID 10133885Pyridine-2-carboxylic acid 4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzylamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Using General procedure H: Reaction of 8-amino-5,6,7,8-tetrahydroquinoline (148 mg, 1.00 mmol) with methanesulfonic acid 4-{[(pyridine-2-carbonyl)-amino]-methyl}-benzyl ester (214 mg, 0.67 mmol) for 3 h at room temperature followed by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH 48:1:1) gave AMD9397 (81 mg, 33%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 1.72-1.83 (m, 2H), 2 00-2.06 (m, 1H), 2.16-2.20 (m, 1H), 2.75-2.83 (m, 2H), 3.82-3.84 (m, 1H), 3.88 (d, 1H), J=13.2 Hz), 3.98 (d, 1H, J=12.9 Hz), 4.65 (d, 2H, J=6.0 Hz), 7.05-7.06 (m, 1H), 7.32-7.42 (m, 6H), 7.85 (ddd, 1H, J=7.8, 7.8, 1.8 Hz), 8.23 (d, 1H, J=7.8 Hz), 8.34 (br s, 1H), 8.37 (d, 1H, J=3.3 Hz), 8.52 (d, 1H, J=3.9 Hz). 13C NMR (75.5 MHz, CDCl3) δ 20.05, 29.00, 29.24, 43.68, 51.85, 57.85, 122.19, 122.70, 126.56, 128.37 (2C), 129.01 (2C), 132.83, 137.07, 137.23, 137.73, 140.41, 147.20, 148.46, 150.23, 157.82, 164.57. ES-MS m/z 373 (M+H). Anal. Calcd. for C23 H24N4O•0.3 H2O: C, 73.11; H, 6.56; N, 14.83. Found: C, 72.98; H, 6.58; N, 14.63.

後処理

  1. customgave AMD9397 (81 mg, 33%) as a yellow oil

出典と根拠

ORDレコード
ord-cba741b13bda4b52a965a27f887e3bc7
出典データセット
uspto-grants-2004_12
特許番号
US06835731B2

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