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Aniline → HCID 69748887, Verbindung

HRID 2301038
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2301038
Cl.CN(C)CCCN=C=NCC.[Cl:13][C:14]1[CH:19]=[C:18]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29](O)=[O:30])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:17]=[CH:16][C:15]=1[NH:32][C:33](=[O:41])[C@:34]([OH:40])([CH3:39])[C:35]([F:38])([F:37])[F:36].[NH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:13][C:14]1[CH:19]=[C:18]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([NH:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:30])=[CH:25][CH:24]=2)(=[O:21])=[O:22])[CH:17]=[CH:16][C:15]=1[NH:32][C:33](=[O:41])[C@:34]([OH:40])([CH3:39])[C:35]([F:38])([F:37])[F:36]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6115AnilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54539434HCID 54539434, Verbindung

Produkt 1

HCID 69748887HCID 69748887, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.195 g) was added to a solution of 4-(dimethylamino)pyridine (0.25 g), (R)-N-[2-chloro-4-(4-carboxyphenyl-sulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 121) (0.317 g) and aniline (0.075 ml) in DCM (30 ml) and the mixture was stirred for 6 days. Solvent was then removed by evaporation and the residue was partitioned between ethyl acetate (50 ml) and dilute aqueous hydrochloric acid (25 ml). The aqueous layer was further extracted with ethyl acetate (50 ml). The organic extracts were combined, washed with brine and dried. Volatile material was removed by evaporation and the residue was purified by chromatography eluting with 40% ethyl acetate/hexane to give the title compound (0.1 79 g) as solid. NMR (CDCl3+DMSO-δ6): 1.59 (s, 3H), 7.03 (t, 1H), 7.25 (t, 2H), 7.48 (brs, 1H), 7.64 (d, 2H), 7.78 (dd, 1H), 7.92 (m, 3H), 8.06 (d, 2H), 8.56 (d 1H), 9.72 (s, 1H), 9.9 (s, 1H); MS (ESP−): 525.

Aufarbeitung

  1. customSolvent was then removed by evaporation
  2. customthe residue was partitioned between ethyl acetate (50 ml) and dilute aqueous hydrochloric acid (25 ml)
  3. extractionThe aqueous layer was further extracted with ethyl acetate (50 ml)
  4. washwashed with brine
  5. customdried
  6. customVolatile material was removed by evaporation
  7. customthe residue was purified by chromatography
  8. washeluting with 40% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-aa562a61c60e4527bff6193ee5abc385
Quelldatensatz
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06498275B1

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