Thionyl Chloride → N-((9H-pyrido[3,4-b]indol-1-yl)methyl)-N-(4-aminobutyl)-5,6,7,8-tetrahydroquinolin-8-amine tetrahydrochloride

HRID 628670ノート

反応式

HRID 628670 の反応式
[C:1]1([CH2:14][N:15]([CH:28]2[C:37]3[N:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH2:31][CH2:30][CH2:29]2)[CH2:16][CH2:17][CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH:4]=[CH:3][N:2]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.S(Cl)([Cl:40])=O>CO>[ClH:40].[ClH:40].[ClH:40].[ClH:40].[C:1]1([CH2:14][N:15]([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH:28]2[C:37]3[N:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH2:31][CH2:30][CH2:29]2)[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH:4]=[CH:3][N:2]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 59176352tert-butyl 4-(((9H-pyrido[3,4-b]indol-1-yl)methyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)butylcarbamate

生成物 1

HCID 68715314N-((9H-pyrido[3,4-b]indol-1-yl)methyl)-N-(4-aminobutyl)-5,6,7,8-tetrahydroquinolin-8-amine tetrahydrochloride収率 80%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of tert-butyl 4-(((9H-pyrido[3,4-b]indol-1-yl)methyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)-butylcarbamate, 4, (0.12 g, 0.24 mmol) in methanol (5 mL) was treated with thionyl chloride (1 mL) at room temperature. The resulting mixture was stirred for 30 min. The reaction mixture was then concentrated and dried under reduced pressure to afford 0.11 g (80% yield) of the desired product A: 1H NMR (400 MHz, d6-DMSO) δ 13.49 (bs, 1H), 8.80-8.41 (m, 3H), 8.00-7.82 (m, 3H), 7.80 (d, J=8.0 Hz, 1H), 7.78-7.70 (m, 1H), 7.39 (t, J=7.2 Hz, 1H), 4.95-4.85 (m, 1H), 4.68-4.50 (m, 2H), 2.98-2.82 (m, 2H), 2.61-2.50 (m, 2H), 2.47-2.35 (m, 3H), 2.12-1.94 (m, 2H), 1.80-1.30 (m, 5H); ESI+ MS: m/z (rel intensity) 400.2 (100, [M+H]+).

後処理

  1. concentrationThe reaction mixture was then concentrated
  2. customdried under reduced pressure

出典と根拠

ORDレコード
ord-0c31b96b3bcb4f5082f58e81d0128eb9
出典データセット
uspto-grants-2016_04
特許番号
US09314468B2

反応ノート

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