Aniline → HC-030031

HRID 1942103

Reaktionsgleichung

Reaktionsgleichung von HRID 1942103
[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([OH:17])=O)[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].CCN(C(C)C)[CH:21]([CH3:23])[CH3:22].[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CCN=C=NCCCN(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:2][N:1]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([CH:21]([CH3:23])[CH3:22])=[CH:30][CH:29]=3)=[O:17])[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4]

Komponenten

8

Edukt 4

HCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69550AcefyllineHCID 81531Diisopropylethylamine

Produkt 1

HCID 1150897HC-030031Ausbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the suspension of theophylline-7-acetic acid (101, 32.5 g, 0.136 mol) in anhydrous DMF (400 mL), was added DIPEA (54 mL, 0.31 mol) at 0° C. The neat aniline (102, 20.4 mL, 0.143 mol) was added followed by addition of DMAP (19.2 g, 0.16 mol) and EDCI (30.1 g, 0.16 mol). The reaction mixture was warmed to room temperature over 18 h, then stirred at 40-43° C. for 1.5 days. The reaction mixture was diluted with CH2Cl2 (1.8 L), washed with H2O (0.7 L), 10% citric acid (0.5 L), NaHCO3 (saturated, 0.6 L), brine, dried over Na2SO4 and concentrated in vacuo and crystallized from ethyl acetate/hexanes to yield compound 200 (41%, 19.8 g): MS (APCI) m/z: 356.2 [M+H]+. Anal. Calcd. for C18H21N5O3: C, 60.83; H, 5.96; N, 19.71; Found: C, 60.53; H, 5.97; N, 19.76.

Aufarbeitung

  1. washwashed with H2O (0.7 L), 10% citric acid (0.5 L), NaHCO3 (saturated, 0.6 L), brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customcrystallized from ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d6ab7241b66c427387d16cc580457dd9
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389529B2

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