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4-Methylmorpholine → Methyl N-({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)-L-serinate

HRID 1624138
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1624138
[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.F[B-](F)(F)F.N1(O[C+](N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.[CH3:54][O:55][C:56](=[O:61])[C@H:57]([CH2:59][OH:60])[NH2:58]>CN(C=O)C.O>[F:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:2]([F:1])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:58][C@H:57]([C:56]([O:55][CH3:54])=[O:61])[CH2:59][OH:60])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1
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Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 867178728-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acidHCID 178484679HCID 178484679, Verbindung

Produkt 1

HCID 86718203Methyl N-({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)-L-serinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

500 mg (1.57 mmol) of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid Example 6A, 756 mg (2.36 mmol) of (benzotriazol-1-yloxy)bisdimethylaminomethylium fluoroborate (TBTU) and 794 mg (7.89 mmol) of 4-methylmorpholine were initially charged in 3 ml of DMF. After 10 min at RT, 293 mg (1.89 mmol) of (5)-serine methyl ester hydrochloride were added and the mixture was stirred at RT overnight. About 80 ml of water were added to the reaction solution, and the precipitate formed was stirred for another 30 min, filtered off, washed thoroughly with cold diethyl ether and dried under high vacuum overnight. This gave 601 mg of the target compound (89% of theory, purity 98%).

Aufarbeitung

  1. customthe precipitate formed
  2. stirringwas stirred for another 30 min
  3. filtrationfiltered off
  4. washwashed thoroughly with cold diethyl ether
  5. customdried under high vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-d121d74d17c4454f87a0c52b402a0670
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08778964B2

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