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

HRID 246728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246728
[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH:27]([F:29])[F:28])[CH:24]=4)[N:19]([CH2:30][CH2:31][C:32](=[O:34])[CH3:33])[N:18]=3)=[CH:15][N:16]=[C:11]2[N:10]([C:35]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[NH4+].[Cl-]>CO>[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH:27]([F:28])[F:29])[CH:24]=4)[N:19]([CH2:30][CH2:31][CH:32]([OH:34])[CH3:33])[N:18]=3)=[CH:15][N:16]=[C:11]2[N:10]([C:35]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:9]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 71280886N-tert-butyl-2-(5-(difluoromethoxy)-1-(3-oxobutyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Produkt 1

HCID 71280582N-tert-butyl-2-(5-(difluoromethoxy)-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-tert-butyl-2-(5-(difluoromethoxy)-1-(3-oxobutyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (0.156 mmol) in MeOH (5 mL) was added NaBH4 (30 mg, 0.78 mmol) at 0° C. The mixture was warmed at room temperature and stirred for 1 hour. Aqueous NH4Cl solution was added to the mixture and product extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude product was used in the next step without purification. MS: (M+H)+=715.

Aufarbeitung

  1. extractionextracted with EtOAc (3×10 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe crude product was used in the next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-4b20e1df571e4517b749c658ce7242a3
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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