4-Morpholinecarbonyl chloride → HCID 59375076, Verbindung

HRID 1811128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811128
[N:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[C:29]2[C:28]3[C:23](=[CH:24][C:25]([OH:30])=[CH:26][CH:27]=3)[NH:22][C:21]=2[C:20]([C:31]([NH2:33])=[O:32])=[CH:19][CH:18]=1>N1C=CC=CC=1.CCOC(C)=O>[N:1]1([C:7]([O:30][C:25]2[CH:26]=[CH:27][C:28]3[C:29]4[C:21](=[C:20]([C:31](=[O:32])[NH2:33])[CH:19]=[CH:18][C:17]=4[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[F:10])[NH:22][C:23]=3[CH:24]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 848104-Morpholinecarbonyl chloride2×HCID 59375146HCID 59375146, Verbindung

Produkt 1

HCID 59375076HCID 59375076, VerbindungAusbeute 31,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Morpholine-4-carbonyl chloride (11.29 mg, 0.075 mmol) was added to a solution of 4-(2-fluorophenyl)-7-hydroxy-9H-carbazole-1-carboxamide (Example 40-1, 18.6 mg, 0.058 mmol) in pyridine (1 mL). After 22 h at rt, additional morpholine-4-carbonyl chloride (11.29 mg, 0.075 mmol) was added. After 15 h, the mixture was diluted with EtOAc (30 mL), washed with water (10 mL) and brine (5 mL), and dried and concentrated. The residue was purified by preparative HPLC to provide 8-carbamoyl-5-(2-fluorophenyl)-9H-carbazol-2-yl morpholine-4-carboxylate as a white solid (7.9 mg, 27%). 1H NMR (400 MHz, chloroform-d) δ 9.94 (1 H, br. s.), 7.41-7.65 (3 H, m), 7.33 (2 H, t, J=8.14 Hz), 7.20 (1 H, d, J=8.58 Hz), 6.92-7.15 (4 H, m), 6.73 (1 H, dd, J=8.58, 1.98 Hz), 3.80 (4 H, t, J=4.62 Hz), 3.67-3.76 (2 H, m), 3.62 (2H, br. s.). Mass spectrum m/z 434.0 (M+H)+.

Aufarbeitung

  1. waitAfter 15 h
  2. washwashed with water (10 mL) and brine (5 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-e132238196294f76a78ce359a9806f7c
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362065B2

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