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4-Methylmorpholine → HCID 86718183, Verbindung

HRID 1624100
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1624100
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16](O)=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.Cl.[NH2:25][C@H:26]([C:31]([O:33][CH3:34])=[O:32])[CH2:27][CH2:28][CH2:29][CH3:30].F[B-](F)(F)F.CN([CH+]N(C)C)C.CN1CCOCC1>ClCCl>[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:25][C@H:26]([C:31]([O:33][CH3:34])=[O:32])[CH2:27][CH2:28][CH2:29][CH3:30])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 14039065methyl (2S)-2-aminohexanoate hydrochlorideHCID 867178728-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acidHCID 178484182HCID 178484182, Verbindung

Produkt 1

HCID 86718183HCID 86718183, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

500 mg of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid (Example 6A; 1.57 mmol, 1 equivalent) were initially charged in 10 ml of anhydrous dichloromethane, and 313 mg of methyl L-norleucinate hydrochloride (1.73 mmol, 1.1 equivalents), 554 mg of benzotriazol-1-yloxy)bisdimethylaminomethylium fluoroborate (TBTU; 1.73 mmol, 1.1 equivalents) and 0.864 ml of 4-methylmorpholine (7.85 mmol, 5 equivalents) were added in succession. The reaction mixture was stirred at room temperature for 4 h. The mixture was then diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate solution, with water and finally with saturated aqueous sodium chloride solution, dried and concentrated. The residue obtained was chromatographed on a 100 g silica gel cartridge (Biotage Isolera; cyclohexane/ethyl acetate gradient as mobile phase). This gave 644 mg of the target compound (91% of theory).

Aufarbeitung

  1. washwashed with saturated aqueous sodium bicarbonate solution, with water and finally with saturated aqueous sodium chloride solution
  2. customdried
  3. concentrationconcentrated
  4. customThe residue obtained
  5. customwas chromatographed on a 100 g silica gel cartridge (Biotage Isolera; cyclohexane/ethyl acetate gradient as mobile phase)

Quellen und Nachweise

ORD-Eintrag
ord-7f6eaa1fcae548abb1b1c409bfeeeaae
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08778964B2

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