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Diisopropylcarbodiimide → 1-[4-(3-Cyclopentyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxymethyl)-phenyl]-1-pyrrolidin-yl-methanone

HRID 1714940
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1714940
[CH:1]1([N:6]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([O:17][CH2:18][C:19]4[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=4)[CH:15]=[CH:16][C:9]=3[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N=C=NC(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.[NH:48]1[CH2:52][CH2:51][CH2:50][CH2:49]1>ClCCl.CN(C)C=O>[CH:1]1([N:6]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([O:17][CH2:18][C:19]4[CH:27]=[CH:26][C:22]([C:23]([N:48]5[CH2:52][CH2:51][CH2:50][CH2:49]5)=[O:24])=[CH:21][CH:20]=4)[CH:15]=[CH:16][C:9]=3[CH2:8][CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 12734DiisopropylcarbodiimideHCID 31268PyrrolidineHCID 27960291-Hydroxybenzotriazole hydrateHCID 103614874-(3-Cyclopentyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxymethyl)-benzoic acid

Produkt 1

HCID 104321781-[4-(3-Cyclopentyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxymethyl)-phenyl]-1-pyrrolidin-yl-methanone

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-(3-Cyclopentyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxymethyl)-benzoic acid (E89) (0.201 mg, 0.55 mmol)), 1,3-diisopropylcarbodiimide (44 μl, 0.6 mmol) and 1-hydroxybenzotriazole hydrate (82 mg, 0.6 mmol) were dissolved in a mixture of dichloromethane (2 ml) and dimethyl formamide (1 ml). After stirring at room temperature for 0.5 hours, pyrrolidine (41 μl, 0.5 mmol) was added and the resulting mixture was allowed to stir for 16 hours. The crude reaction was applied to a SCX ion exchange cartridge (Varian bond-elute, 5 g) and washed with methanol and then a mixture of 0.880 ammonia:methanol (1:9). The combined basic fractions were concentrated in vacuo, and the resulting residue was purified by column chromatography eluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (1:9:90) to afford the title compound (E90); MS (ES+) m/e 419 [M+H]+.

Aufarbeitung

  1. stirringto stir for 16 hours
  2. customThe crude reaction
  3. washwashed with methanol
  4. additiona mixture of 0.880 ammonia:methanol (1:9)
  5. concentrationThe combined basic fractions were concentrated in vacuo
  6. customthe resulting residue was purified by column chromatography
  7. washeluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (1:9:90)

Quellen und Nachweise

ORD-Eintrag
ord-96ad29d255fd48a8a2ec52a3c9df4f0c
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07799773B2

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