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

HRID 628670노트

반응식

HRID 628670 반응식
[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

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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]+).

후처리

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

출처 및 근거

ORD 기록
ord-0c31b96b3bcb4f5082f58e81d0128eb9
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09314468B2

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