Acetic Acid → 5-(3-{[2-(tert-Butoxycarbonyl-methyl-amino)-ethylamino]-methyl}-4-fluoro-phenyl)-indazole-1-carboxylic acid tert-butyl ester

HRID 1864793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1864793
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[C:19]([O:23][C:24]([N:26]1[C:34]2[C:29](=[CH:30][C:31]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[C:37]([CH:42]=O)[CH:36]=3)=[CH:32][CH:33]=2)[CH:28]=[N:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].[C:44]([O:48][C:49](=[O:55])[N:50]([CH2:52][CH2:53][NH2:54])[CH3:51])([CH3:47])([CH3:46])[CH3:45]>ClC(Cl)C.O>[C:19]([O:23][C:24]([N:26]1[C:34]2[C:29](=[CH:30][C:31]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[C:37]([CH2:42][NH:54][CH2:53][CH2:52][N:50]([C:49]([O:48][C:44]([CH3:47])([CH3:45])[CH3:46])=[O:55])[CH3:51])[CH:36]=3)=[CH:32][CH:33]=2)[CH:28]=[N:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 2756424N-Boc-N-methylethylenediamineHCID 5049666Sodium triacetoxyborohydrideHCID 866164695-(4-Fluoro-3-formylphenyl)-indazole-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 687486135-(3-{[2-(tert-Butoxycarbonyl-methyl-amino)-ethylamino]-methyl}-4-fluoro-phenyl)-indazole-1-carboxylic acid tert-butyl esterAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

Sodium triacetoxyborohydride (250 mg, 1.2 mmol) and acetic acid (42 mg, 1.2 mmol) were added to a mixture of 5-(4-fluoro-3-formylphenyl)-indazole-1-carboxylic acid tert-butyl ester (270 mg, 0.8 mmol) and (2-amino-ethyl)-methyl-carbamic acid tert-butyl ester (210 mg, 1.2 mmol) in 8 mL of dichloroethane. The mixture was stirred at ambient temperature overnight, and then it was diluted with water, the layers were separated and the aqueous phase was extracted with dichloromethane. The combined organic layers were washed with sequentially with water, saturated sodium bicarbonate solution and water, dried over magnesium sulfate, filtered and concentrated to leave the crude product. Chromatography (elution with methanol/dichloromethane) provided 400 mg of product. LC/MS: Retention time, 2.66 min; (M+H)=499.

Aufarbeitung

  1. customthe layers were separated
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. washThe combined organic layers were washed with sequentially with water, saturated sodium bicarbonate solution and water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto leave the crude product
  8. washChromatography (elution with methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-82d14490e8494b3babc895eacd83bee1
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625889B2

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