Morpholine → methyl 2-(2-acetylphenyl)-3-cyclohexyl-1H-indole-6-carboxylate

HRID 1453363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1453363
[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[CH:17][C:18]=4[N:9]3CC=C[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:22]1[C:32]2C3=CC4C=CC(C(O)=O)=CC=4N3C=CC[C:26]=2[CH:25]=[CH:24][CH:23]=1.C1C2C3=CC4C=C[C:58]([C:61](O)=[O:62])=CC=4N3CC(C(O)=O)=CC=2C=CC=1.[CH3:67]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.N1CCOCC1>CS(C)=O>[C:61]([C:5]1[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=1[C:10]1[NH:9][C:18]2[C:13]([C:12]=1[CH:22]1[CH2:32][CH2:26][CH2:25][CH2:24][CH2:23]1)=[CH:14][CH:15]=[C:16]([C:19]([O:21][CH3:67])=[O:20])[CH:17]=2)(=[O:62])[CH3:58]

Komponenten

8

Edukt 6

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 665887027H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylic acidHCID 666396797H-indolo[2,1-a][2]benzazepine-10-carboxylic acidHCID 685639665H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

Produkt 1

HCID 58765163methyl 2-(2-acetylphenyl)-3-cyclohexyl-1H-indole-6-carboxylateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-5-methyl-6-(4-morpholinylcarbonyl)-, methyl ester. To a solution of 7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylic acid, 13-cyclohexyl-5-methyl-, 10-methyl ester (120 mg, 0.28 mmol) in DMSO (3.0 mL), TBTU (135 mg, 0.42 mmol) and DIPEA (0.244 mL, 1.4 mmol) were added. The reaction mixture was stirred at rt for 15 min. Then morpholine (0.037 mL, 0. 42 mmol) was added and the reaction mixture was stirred at rt for overnight. It was then concentrated under reduced pressure and the residue was purified by Prep. reverse phase HPLC to give the title compound as a white solid, (115 mg, 82% yield). MS m/z 499(MH+); 1H NMR (500 MHz, CD3OD) δ ppm Compound exists as a complex mixture of rotamers.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at rt for overnight
  2. concentrationIt was then concentrated under reduced pressure
  3. customthe residue was purified by Prep

Quellen und Nachweise

ORD-Eintrag
ord-8a9357df51444150a0e12e23db425a44
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07473688B2

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