Ammonium Chloride → N-(1-(tert-Butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-fluoro-1-(3-hydroxybutyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246777

Reaktionsgleichung

Reaktionsgleichung von HRID 246777
[Si:1]([O:8][CH2:9][C:10]([NH:13][C:14]([C:16]1[C:20]2=[N:21][C:22]([C:25]3[C:33]4[C:28](=[CH:29][C:30]([F:34])=[CH:31][CH:32]=4)[N:27]([CH2:35][CH2:36][C:37](=[O:39])[CH3:38])[N:26]=3)=[CH:23][N:24]=[C:19]2[N:18]([C:40]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:17]=1)=[O:15])([CH3:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].[NH4+].[Cl-]>CO>[Si:1]([O:8][CH2:9][C:10]([NH:13][C:14]([C:16]1[C:20]2=[N:21][C:22]([C:25]3[C:33]4[C:28](=[CH:29][C:30]([F:34])=[CH:31][CH:32]=4)[N:27]([CH2:35][CH2:36][CH:37]([OH:39])[CH3:38])[N:26]=3)=[CH:23][N:24]=[C:19]2[N:18]([C:40]([C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:17]=1)=[O:15])([CH3:11])[CH3:12])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 71279418N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-fluoro-1-(3-oxobutyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Produkt 1

HCID 71279489N-(1-(tert-Butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-fluoro-1-(3-hydroxybutyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-fluoro-1-(3-oxobutyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (40 mg, 0.05 mmol) in MeOH (5 mL) was added NaBH4 (10 mg, 0.25 mmol) at 0° C. The mixture was stirred at room temperature for 1 hour. NH4Cl (aqueous) was added to the mixture to quench the reaction. The mixture was extracted with EtOAc (3×5 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude was used into the next step without purification. LCMS: (M+H)+=797.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with EtOAc (3×5 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe crude was used into the next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-7ee04c01e116446b9e6302262a959d9b
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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