Hydrochloric Acid → {3-[N-({6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]phenyl}acetic acid

HRID 1099690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1099690
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([C:14]2[CH:15]=[C:16]([CH2:20][C:21]([O:23]C)=[O:22])[CH:17]=[CH:18][CH:19]=2)([CH3:13])=[O:12])=[O:9])=[CH:4][C:3]=1[C:25]#[C:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34]([C:36]2[N:40]([CH3:41])[N:39]=[C:38]([CH3:42])[CH:37]=2)=[O:35])[CH:28]=1.[OH-].[Na+].Cl>CO.O.[Cl-].[Na+].O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([C:14]2[CH:15]=[C:16]([CH2:20][C:21]([OH:23])=[O:22])[CH:17]=[CH:18][CH:19]=2)([CH3:13])=[O:12])=[O:9])=[CH:4][C:3]=1[C:25]#[C:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34]([C:36]2[N:40]([CH3:41])[N:39]=[C:38]([CH3:42])[CH:37]=2)=[O:35])[CH:28]=1

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57657942methyl {3-[N-({6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]phenyl}acetate

Produkt 1

HCID 57657920{3-[N-({6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]phenyl}acetic acidAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A solution of methyl {3-[N-({6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]phenyl}acetate (13 mg, 0.021 mmol) and 1.0M NaOH (0.171 ml, 0.171 mmol) in 2.0 ml MeOH and 0.1 ml H2O was stirred at room temperature for 1 hour 10 minutes. The pH of the mixture was adjusted to pH 4 using 10% HCl, brine added, and the aqueous extracted with EtOAc. The combined EtOAc layers were washed with brine, dried with anhydrous Na2SO4 and rotary evaporated. The white solid was triturated with hot EtOAc to give white solid (11 mg, 92%).

Aufarbeitung

  1. additionadded
  2. extractionthe aqueous extracted with EtOAc
  3. washThe combined EtOAc layers were washed with brine
  4. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
  5. customThe white solid was triturated with hot EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-2d7f1b3108de4393aece9795cacedfde
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143410B2

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