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Dimethylformamide → HCID 178509601, Verbindung

HRID 351101
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 351101
[Cl:1][C:2]1[CH:19]=[C:18]([CH2:20][C:21](=O)[C:22]2[CH:26]=[C:25]([C:27](=[O:32])C(Cl)(Cl)Cl)[NH:24][CH:23]=2)[CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1C(=O)C2C(=CC=CC=2)C1=O.[Cl:34][C:35]1[CH:36]=[C:37](NCCO)[CH:38]=[CH:39][C:40]=1[F:41].[C:46]([CH:50]([N:54](C)C)N(C)C)(C)(C)C.[OH2:57].[NH2:58]N.C[N:61]([CH:63]=O)C>C1COCC1.C(O)C>[Cl:34][C:35]1[CH:36]=[C:37]([CH:50]([NH:54][C:27]([C:25]2[NH:24][CH:23]=[C:22]([C:21]3[C:20]([C:18]4[CH:17]=[CH:16][C:3]([CH2:4][NH2:5])=[C:2]([Cl:1])[CH:19]=4)=[CH:63][NH:61][N:58]=3)[CH:26]=2)=[O:32])[CH2:46][OH:57])[CH:38]=[CH:39][C:40]=1[F:41]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 6228DimethylformamideHCID 24654Hydrazine hydrate (1:1)HCID 129886122-(2-Chloro-4-{2-oxo-2-[5-(2,2,2-trichloro-acetyl)-1H-pyrrol-3-yl-]-ethyl}-benzyl)-isoindole-1,3-dioneHCID 15731881Tert-butyl bis(dimethylamino)-methaneHCID 22349678N-2-hydroxyethyl-3-chloro-4-fluoroaniline

Produkt 1

HCID 178509601
HCID 178509601, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of compound 10 (1.0 mmol) in DMF (5 mL) was added (S) 3-chloro-4-fluoro phenyl glycinol (1.2 mmol), then stirred for 15 h. The solvent was concentrated under vacuum. To the residue (1.0 mmol) in THF (1 mL) was added tert-butyl bis(dimethylamino)-methane (1 mL, 5 mmol). The mixture was stirred for 15 h at 50° C. and then concentrated under vacuum. To the residue (1 mmol) was added C2H5OH (5 mL) and hydrazine hydrate (1 mL, 20 mmol). The mixture was refluxed for 3 h and cooled to room temperature. The solvents were removed under vacuum and the crude products were purified from preparatory HPLC. This afforded the product 11 as a white solid. 1HNMR (CD3OD) 7.6 (s, 1H), 7.4 (s, 1H), 7.2–7.4 (m, 3H), 7.1–7.2 (m, 1H), 7.0 (t, 1H), 6.8 (d, 2H), 4.9 (t, 1H), 4.1 (s, 2H), 3.6 (dd, 2H).

Aufarbeitung

  1. concentrationThe solvent was concentrated under vacuum
  2. stirringThe mixture was stirred for 15 h at 50° C.
  3. concentrationconcentrated under vacuum
  4. temperatureThe mixture was refluxed for 3 h
  5. customThe solvents were removed under vacuum
  6. customthe crude products were purified from preparatory HPLC

Quellen und Nachweise

ORD-Eintrag
ord-7580c8bafbfc42b0b08504546fd27780
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07183307B2

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