1-(3-(Pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-amine → 5-methyl-N-(1-(3-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide

HRID 1922528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922528
[N:1]1([CH2:6][CH2:7][CH2:8][N:9]2[C:18]3[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH2:10]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.I.[CH3:21][C:22]1[S:26][C:25]([C:27](SC)=[NH:28])=[CH:24][CH:23]=1>C(O)C.O.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:21][C:22]1[S:26][C:25]([C:27](=[NH:28])[NH:19][C:15]2[CH:14]=[C:13]3[C:18](=[CH:17][CH:16]=2)[N:9]([CH2:8][CH2:7][CH2:6][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:10][CH2:11][CH2:12]3)=[CH:24][CH:23]=1

Komponenten

6

Edukt 2

HCID 533923491-(3-(Pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-amineHCID 67493060Methyl 5-methylthiophene-2-carbimidothioate hydroiodide

Produkt 1

HCID 1784256255-methyl-N-(1-(3-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamideAusbeute 57,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-(3-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-amine (115 mg, 0.443 mmol) in ethanol (6 ml) was added methyl 5-methylthiophene-2-carbimidothioate hydroiodide (265 mg, 0.887 mmol). The resulting suspension was stirred overnight at room temperature. The mixture was then diluted with water and sodium carbonate and extracted with dichloromethane. The combined organics were dried, filtered and concentrated, then chromatographed on silica gel with ethyl acetate, followed by 5-10% (2M NH3 in MeOH) in dichloromethane as eluent to give the desired 5-methyl-N-(1-(3-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide (98 mg, 0.256 mmol, 57.8% yield). 1H NMR (DMSO-d6) δ 7.45 (d, J=3.3 Hz, 1H), 6.74 (d, J=2.4 Hz, 1H), 6.53 (m, 2H), 6.45 (s, 1H), 6.13 (brs, 2H), 3.26-3.16 (m, 4H), 2.68-2.63 (m, 2H), 2.43-2.39 (m, 6H), 2.41 (s, 3H), 1.86-1.82 (m, 2H), 1.68-1.64 (m, 6H). ESI-MS (m/z, %) 383 (MH+, 39), 272 (49), 192 (100). ESI-HRMS calculated for C22H31N4S (MH+), calculated: 383.2264, observed:

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. customThe combined organics were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-744c698cf3164544bfe14603f9c956ab
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173813B2

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