4-Methylmorpholine → HCID 86718177, Verbindung

HRID 1624123

Reaktionsgleichung

Reaktionsgleichung von HRID 1624123
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15]([C:19]([OH:21])=O)=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:22][C@H:23]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:24][OH:25].CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>ClCCl>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15]([C:19]([NH:22][C@H:23]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:24][OH:25])=[O:21])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6994402(R)-2-Aminohexan-1-olHCID 98822062-Methyl-8-(phenylmethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid

Produkt 1

HCID 86718177HCID 86718177, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Under argon, 4 g (14.17 mmol) of 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid, 1.83 g (15.59 mmol) of (R)-(−)-2-aminohexanol and 7.166 g (70.85 mmol) of 4-methylmorpholine were suspended in 28 ml of dichloromethane. 5 g (15.59 mmol) of TBTU were then added, and the mixture was stirred at room temperature overnight. After 16 h, the mixture was diluted with 200 ml of dichloromethane and washed with 10% strength aqueous citric acid solution, with water and with saturated aqueous sodium chloride solution. The organic phase was concentrated and the residue obtained was purified on a silica gel cartridge (mobile phase dichloromethane:methanol=100:3). Concentration of the product fractions thus gave 3.83 g (71% of theory) of 8-(benzyloxy)-N-[(2R)-1-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Aufarbeitung

  1. waitAfter 16 h
  2. washwashed with 10% strength aqueous citric acid solution, with water and with saturated aqueous sodium chloride solution
  3. concentrationThe organic phase was concentrated
  4. customthe residue obtained
  5. customwas purified on a silica gel cartridge (mobile phase dichloromethane:methanol=100:3)

Quellen und Nachweise

ORD-Eintrag
ord-789816e5fb584b67bd6157953815c035
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778964B2

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