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1-(2-(1-Methylpyrrolidin-2-yl)ethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-amine → HCID 178480163, Verbindung

HRID 1922443
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1922443
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2[CH:16]=[C:17]([NH2:20])[CH:18]=[CH:19][C:10]1=2.CN(CCN1C2C(=CC=C([NH:44][C:45]([C:47]3[S:48][CH:49]=[CH:50][CH:51]=3)=N)C=2)CCC1)C(=O)OC1C=CC=CC=1>C(O)C.C([O-])(O)=O.[Na+]>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2[CH:16]=[C:17]([NH:20][C:45]([C:47]3[S:48][CH:49]=[CH:50][CH:51]=3)=[NH:44])[CH:18]=[CH:19][C:10]1=2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 674928321-(2-(1-Methylpyrrolidin-2-yl)ethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-amineHCID 178484202HCID 178484202, Verbindung

Produkt 1

HCID 178480163HCID 178480163, VerbindungAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 516892Sodium Bicarbonate
Lösungsmittel

Versuchsvorschrift

A solution of 4 (170 mg, 0.62 mmol) in dry ethanol (15 mL) was treated with 5 (0.355 g, 1.24 mmol) and stirred for overnight (17 h) at room temperature. The reaction mixture was diluted with saturated NaHCO3 solution (100 mL) and extracted with CH2Cl2 (2×50 mL). The combined organic fractions were washed with brine (50 mL), dried (Na2SO4) and concentrated. The crude product was purified by dry column chromatography (MeOH:CH2Cl2, 2:98 followed by 2 N NH3 in MeOH:CH2Cl2 3:97) to give compound 45 (177 mg, 74%) as a yellow solid. 1H-NMR (DMSO-d6) δ: 1.38-1.69 (m, 8H), 1.83-1.89 (m, 2H), 2.02-2.12 (m, 2H), 2.19 (s, 3H), 2.65-2.68 (m, 2H), 2.80-3.12 (m, 5H), 6.32 (brs, 2H), 6.62-6.64 (m, 2H), 6.85-6.88 (d, 1H, J=8.9 Hz), 7.06-7.09 (t, 1H, J=3.8 Hz), 7.56-7.58 (d, 1H, J=5.0 Hz), 7.69-7.71 (d, 1H, J=3.6 Hz); ESI-MS (m/z, %): 383 (MH+, 33), 192 (100), 142 (51). ESI-HRMS calculated for C22H30N4S (MH+), calculated: 383.2253; observed: 383.2263; HPLC-purity: 93.49% by area.

Aufarbeitung

  1. extractionextracted with CH2Cl2 (2×50 mL)
  2. washThe combined organic fractions were washed with brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product was purified
  6. dry with materialby dry column chromatography (MeOH:CH2Cl2, 2:98 followed by 2 N NH3 in MeOH:CH2Cl2 3:97)

Quellen und Nachweise

ORD-Eintrag
ord-042d6ae12273459baeda772d3de42165
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08173813B2

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