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Sodium Bicarbonate → Benzyl 1-[({2,5-difluoro-4-[(2-{[((S)-3-hydroxypyrrolidin-1-yl)carbonyl]amino}pyridin-4-yl)oxy]phenyl}amino)carbonyl]cyclopropanecarboxylate

HRID 1712682
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1712682
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.[O:7]([C:14]([NH:16][C:17]1[CH:22]=[C:21]([O:23][C:24]2[C:29]([F:30])=[CH:28][C:27]([NH:31][C:32]([C:34]3([C:37]([O:39][CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[O:38])[CH2:36][CH2:35]3)=[O:33])=[C:26]([F:47])[CH:25]=2)[CH:20]=[CH:19][N:18]=1)=O)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>CN1CCCC1=O>[F:47][C:26]1[CH:25]=[C:24]([O:23][C:21]2[CH:20]=[CH:19][N:18]=[C:17]([NH:16][C:14]([N:4]3[CH2:5][CH2:6][C@H:2]([OH:1])[CH2:3]3)=[O:7])[CH:22]=2)[C:29]([F:30])=[CH:28][C:27]=1[NH:31][C:32]([C:34]1([C:37]([O:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)=[O:38])[CH2:36][CH2:35]1)=[O:33]
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Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 2733874(3S)-pyrrolidin-3-olHCID 24788625Benzyl 1-({[4-([2-[(phenoxycarbonyl)amino]pyridin-4-yl}oxy)-2,5-difluorophenyl]amino}carbonyl)cyclopropanecarboxylate

Produkt 1

HCID 59459706Benzyl 1-[({2,5-difluoro-4-[(2-{[((S)-3-hydroxypyrrolidin-1-yl)carbonyl]amino}pyridin-4-yl)oxy]phenyl}amino)carbonyl]cyclopropanecarboxylateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

(S)-3-Hydroxypyrrolidine (0.0577 ml) was added to a mixture of benzyl 1-({[4-({2-[(phenoxycarbonyl)amino]pyridin-4-yl}oxy)-2,5-difluorophenyl]amino}carbonyl)cyclopropanecarboxylate (200 mg) and N-methylpyrrolidinone (4.0 ml) at room temperature under a nitrogen atmosphere, and the mixture was stirred for 2 hours. A saturated aqueous solution of sodium hydrogencarbonate (20 ml) was added to the mixture, and the mixture was stirred for 30 minutes. The precipitated solid was collected by filtration, and the solid was washed with water (20 ml, three times), and the solid was dried by hot air (80° C.) for 1 day to give the title compound (159.0 mg, 81%) as a white solid.

Aufarbeitung

  1. stirringthe mixture was stirred for 30 minutes
  2. filtrationThe precipitated solid was collected by filtration
  3. washthe solid was washed with water (20 ml, three times)
  4. customthe solid was dried by hot air (80° C.) for 1 day

Quellen und Nachweise

ORD-Eintrag
ord-b82b840b79d44db79f8233dc33a61674
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07790885B2

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