1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → CID 59753533

HRID 1693378

Reaktionsgleichung

Reaktionsgleichung von HRID 1693378
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:14][NH2:15])[O:13][CH2:12][CH2:11][O:10]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[Cl:25][C:26]1[CH:27]=[C:28]2[CH:34]=[C:33]([C:35](O)=[O:36])[NH:32][C:29]2=[CH:30][N:31]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([CH2:14][NH:15][C:35]([C:33]3[NH:32][C:29]4=[CH:30][N:31]=[C:26]([Cl:25])[CH:27]=[C:28]4[CH:34]=3)=[O:36])[O:10][CH2:11][CH2:12][O:13]2)=[CH:7][CH:8]=1

Komponenten

7

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 12833653[2-(4-Methoxyphenyl)-[1,3]dioxolan-2-yl]methylamineHCID 446307045-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Produkt 1

HCID 59753533CID 59753533

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of [2-(4-methoxyphenyl)-[1,3]-dioxolan-2-yl]methylamine (Preparation 45, 0.117 g, 0.56 mmol) in dichloromethane (5 mL) was added DIPEA (213 μL, 1.22 mmol), 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 18, 0.100 g, 0.51 mmol) and HOBT (0.076 g, 0.56 mmol). The resulting solution was stirred for 2 min then EDCI (0.117 g, 0.61 mmol) was added and stirring was continued for 18 h at rt. The reaction mixture was partitioned between dichloromethane (30 mL) and water (20 mL) and the layers separated. The aqueous phase was extracted with dichloromethane (3×20 mL) then the combined organics were washed with brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo. Recrystallisation from methanol/dichloromethane gave the title compound as an orange solid. δH (CDCl3): 3.81 (3H, s), 3.84-3.91 (4H, m), 4.05 (2H, m), 6.56 (1H, t), 6.76 (1H, s), 6.89 (2H, d), 7.44 (2H, d), 7.57 (1H, s), 8.68 (1H, s), 9.94 (1H, br s).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 18 h at rt
  3. customThe reaction mixture was partitioned between dichloromethane (30 mL) and water (20 mL)
  4. customthe layers separated
  5. extractionThe aqueous phase was extracted with dichloromethane (3×20 mL)
  6. washthe combined organics were washed with brine (20 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customRecrystallisation from methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-a7ba2dc9dc0d44e38f893b465599b448
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158622B2

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