Sodium borohydride → 1-(2-(2-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenylamino)methyl)-1-trityl-1H-imidazol-4-yl)phenyl)ethanol

HRID 2104980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2104980
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:58][CH:59]([CH3:61])[CH3:60])[C:7]([F:57])=[C:8]([CH:10]([NH:44][C:45]2[CH:50]=[CH:49][C:48]([C:51]3[N:55]=[C:54]([CH3:56])[O:53][N:52]=3)=[CH:47][CH:46]=2)[C:11]2[N:12]([C:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22](=[O:24])[CH3:23])[N:15]=2)[CH:9]=1)[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:58][CH:59]([CH3:60])[CH3:61])[C:7]([F:57])=[C:8]([CH:10]([NH:44][C:45]2[CH:46]=[CH:47][C:48]([C:51]3[N:55]=[C:54]([CH3:56])[O:53][N:52]=3)=[CH:49][CH:50]=2)[C:11]2[N:12]([C:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH:22]([OH:24])[CH3:23])[N:15]=2)[CH:9]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 688129901-(2-(2-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenylamino)methyl)-1-trityl-1H-imidazol-4-yl)phenyl)ethanone

Produkt 1

HCID 688125471-(2-(2-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenylamino)methyl)-1-trityl-1H-imidazol-4-yl)phenyl)ethanolAusbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of Intermediate 111.1 (40 mg, 0.05 mmol) and NaBH4 (5 mg) in 1 mL MeOH was stirred for 0.5 h at rt. The reaction mixture was partitioned between EtOAc and H2O, the organic layer was collected, dried (Na2SO4), filtered and concentrated to afford 30 mg of Intermediate 111.2. LCMS (2 min gradient) RT=1.49 min, 814.4 (M+H).

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc and H2O
  2. customthe organic layer was collected
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c079cd8255874c1696fba433aa16bc12
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576098B2

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