3-(4-(Dimethylamino)cyclohex-1-enyl)-1H-indol-5-amine → HCID 178482648, Verbindung

HRID 2043521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2043521
[CH3:1][N:2]([CH3:19])[CH:3]1[CH2:8][CH2:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH2:18])[CH:16]=3)[NH:11][CH:10]=2)=[CH:5][CH2:4]1.I.CS[C:23]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)=[NH:24]>C(O)C>[CH3:1][N:2]([CH3:19])[CH:3]1[CH2:8][CH2:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:23]([C:25]4[S:26][CH:27]=[CH:28][CH:29]=4)=[NH:24])[CH:16]=3)[NH:11][CH:10]=2)=[CH:5][CH2:4]1

Komponenten

4

Edukt 2

HCID 574744603-(4-(Dimethylamino)cyclohex-1-enyl)-1H-indol-5-amineHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Produkt 1

HCID 178482648HCID 178482648, VerbindungAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of compound 113 (0.18 g, 0.704 mmol) in dry ethanol (10 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.4 g, 1.409 mmol) at room temperature and stirred for 24 h. Solvent was evaporated and crude was diluted with sat. NaHCO3 solution (20 mL) and product was extracted into CH2Cl2 (2×25 mL). The combined CH2Cl2 layer was washed with brine (20 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 1:9) to obtain compound 114 (0.24 g, 90%) as a solid. mp 113-115° C.; 1H NMR (DMSO-d6) δ 1.42-1.53 (m, 1H), 1.97-2.02 (m, 1H), 2.08-2.22 (m, 8H), 2.31-2.60 (m, 3H), 6.03 (s, 1H), 6.21 (brs, 2H), 6.65 (dd, 1H, J=1.2, 8.4 Hz), 7.09 (t, 1H, J=4.2 Hz), 7.20 (s, 1H), 7.28-7.31 (m, 2H), 7.58 (d, 1H, J=4.5 Hz), 7.71 (d, 1H, J=2.7 Hz), 10.88 (s, 1H); ESI-MS m/z (%): 365 (MH+, 39), 320 (38), 183 (76), 160 (100); ESI-HRMS calculated for C21H25N4S (MH+), Calculated: 365.1813; Observed: 365.1794.

Aufarbeitung

  1. customSolvent was evaporated
  2. additioncrude was diluted with sat. NaHCO3 solution (20 mL) and product
  3. extractionwas extracted into CH2Cl2 (2×25 mL)
  4. washThe combined CH2Cl2 layer was washed with brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. customSolvent was evaporated
  7. customcrude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 1:9)

Quellen und Nachweise

ORD-Eintrag
ord-e14e8f6da12a4b70a2bdf053ac911f97
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586620B2

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