Hydrochloric Acid → 1-(4-Cyano-7-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)piperidine-4-carboxylic acid

HRID 17430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17430
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]([O:20]CC)=[O:19])[CH2:14][CH2:13]3)[O:11][C:7]=2[C:6]([N:23]2[CH2:27][CH2:26][C@H:25]([N:28]([CH3:30])[CH3:29])[CH2:24]2)=[C:5]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:4]=1[CH3:37])#[N:2].[OH-].[Na+].Cl>O1CCCC1>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]3)[O:11][C:7]=2[C:6]([N:23]2[CH2:27][CH2:26][C@H:25]([N:28]([CH3:30])[CH3:29])[CH2:24]2)=[C:5]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:4]=1[CH3:37])#[N:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 68584931Ethyl 1-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}piperidine-4-carboxylate

Produkt 1

HCID 685863861-(4-Cyano-7-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)piperidine-4-carboxylic acidAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethyl 1-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}piperidine-4-carboxylate (I-162) (0.26 g, 0.52 mmol) was dissolved in tetrahydrofuran (10 ml), then 1 N sodium hydroxide (0.60 ml, 0.60 mmol) was added. After stirring at room temperature for 19 hours, 1 N sodium hydroxide (0.40 ml, 0.40 mmol) was further added, followed by stirring at room temperature for 24 hours. 1 N Hydrochloric acid (1.00 ml, 1.00 mmol) was added, then the solvent was evaporated away under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol:water=8:3:0.5), then ethanol and a small amount of ether were added, and the insoluble matter was collected by filtration to obtain a colorless solid (0.18 g, 71%).

Aufarbeitung

  1. stirringby stirring at room temperature for 24 hours
  2. customthe solvent was evaporated away under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol:water=8:3:0.5)
  4. additionethanol and a small amount of ether were added
  5. filtrationthe insoluble matter was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-517dcedeb4734de6a7071bc5b7709581
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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