1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-(3-amino-4-fluorophenyl)(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)methanone

HRID 400527

Reaktionsgleichung

Reaktionsgleichung von HRID 400527
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=O.O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[CH2:34]1[NH:39][CH2:38][CH2:37][N:36]2[CH2:40][CH2:41][CH2:42][C@H:35]12>ClCCl.CN(C)C=O.ClCCl>[NH2:1][C:2]1[CH:3]=[C:4]([C:5]([N:39]2[CH2:38][CH2:37][N:36]3[CH2:40][CH2:41][CH2:42][C@@H:35]3[CH2:34]2)=[O:7])[CH:8]=[CH:9][C:10]=1[F:11]

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 753963-Amino-4-fluorobenzoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 7004239(8aR)-Octahydropyrrolo(1,2-a)pyrazine

Produkt 1

HCID 66676376(R)-(3-amino-4-fluorophenyl)(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 22350042dichloromethane N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

To 3-amino-4-fluorobenzoic acid (0.621 g, 4 mmol) and 1-hydroxybenzotriazole hydrate (0.613 g, 4 mmol) in dichloromethane/N,N-dimethylformamide (10:1, 60 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC, 0.621 g, 4 mmol). After 5 minutes, (R)-octahydropyrrolo[1,2-a]pyrazine (0.505 g, 4 mmol) in dichloromethane (1 mL) was added. The mixture was stirred at room temperature overnight. Then the mixture was concentrated. The residue was purified by chromatography on silica gel (dichloromethane, then methanol/dichloromethane=1:10) to give (R)-(3-amino-4-fluorophenyl)(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)methanone: 1H NMR (500 MHz, DMSO-d6) δ ppm 1.25 (m, 1H), 1.60-2.10 (m, 6H), 2.70-3.10 (m, 4H), 3.55-3.70 (m, 1H), 4.40-4.60 (m, 1H), 5.30 (s, 2H), 6.50 (m, 1H), 6.77 (m, 1H), 7.00 (m, 1H); MS (ESI) m/z 264 (M+H)+.

Aufarbeitung

  1. concentrationThen the mixture was concentrated
  2. customThe residue was purified by chromatography on silica gel (dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-78a50519fe824b13a5f863a7acb6edb0
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741899B2

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