Phenyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate → HCID 178480394, Verbindung

HRID 1922427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922427
CN([CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[NH:26])=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1=O)C(=O)OC1C=CC=CC=1.NC1C=[C:36]2[C:41](=CC=1)[N:40]([CH2:44]CN(C)C(=O)OC1C=CC=CC=1)[C:39](=O)[CH2:38]C2>C(O)C.C([O-])(O)=O.[Na+]>[CH3:44][N:40]1[CH2:41][CH2:36][CH:15]([N:14]2[CH2:13][CH2:12][CH2:16][CH2:17][C:18]3[CH:19]=[C:20]([NH:24][C:25]([C:27]4[S:28][CH:29]=[CH:30][CH:31]=4)=[NH:26])[CH:21]=[CH:22][C:23]2=3)[CH2:38][CH2:39]1

Komponenten

5

Edukt 2

HCID 59807067Phenyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamateHCID 178484234Phenyl methyl(2-(2-oxo-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate

Produkt 1

HCID 178480394HCID 178480394, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A solution of compound 8 (321.6 mg, 1.24 mmol) in dry ethanol (10 mL) was treated with compound 6 (707 mg, 2.48 mmol) at room temperature. The reaction mixture was stirred for 16 hours at room temperature then diluted with saturated NaHCO3 solution (50 mL) and extracted with CH2Cl2 (2×50 mL). The combined organic fractions were washed with brine (50 mL), dried (Na2SO4) and concentrated to give a brown residue. The crude product was purified by column chromatography on silica gel (MeOH:CH2Cl2, 2:98 followed by 2 N NH3 in MeOH:CH2Cl2, 4:96 to 5:95) to give compound 39 (374.6 mg, 81.9%) as a yellow residue. 1H-NMR (DMSO-d6) δ 1.56-1.79 (m, 9H), 1.97 (t, 2H, J=10.5 Hz), 2.16 (s, 3H), 2.65 (brs, 2H), 2.80 (d, 2H, J=10.2 Hz), 2.91 (brs, 2H), 3.12 (m, 1H), 6.30 (brs, 2H), 6.59 (m, 2H), 6.89 (d, 1H, J=8.9 Hz), 7.07 (t, 1H, J=4.5 Hz), 7.57 (d, 1H, J=5.1), 7.70 (d, 1H, J=3.5 Hz); ESI-MS (m/z, %) 369 (MH+, 35), 272 (100). ESI-HRMS calculated for C21H29N4S (MH+), calculated: 369.2101; observed: 369.2107; HPLC-purity: 97.31% 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. customto give a brown residue
  6. customThe crude product was purified by column chromatography on silica gel (MeOH:CH2Cl2, 2:98 followed by 2 N NH3 in MeOH:CH2Cl2, 4:96 to 5:95)

Quellen und Nachweise

ORD-Eintrag
ord-cf8f3b2fea60439abbea22bd67a9526c
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173813B2

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