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

HRID 628670Notes

Reaction equation

HRID 628670 reaction equation
[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

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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]+).

Workup

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

Sources & evidence

ORD record
ord-0c31b96b3bcb4f5082f58e81d0128eb9
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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