Glyceraldehyde → HCID 178521766, Verbindung

HRID 1163419

Reaktionsgleichung

Reaktionsgleichung von HRID 1163419
Cl.Cl.Cl.[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]([C:16]3[C:35]([N:36]4[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]4)=[CH:34][C:19]4[NH:20][C:21]([NH:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[C:30]([F:33])([F:32])[F:31])=[N:22][C:18]=4[CH:17]=3)=[O:15])[CH:11]=2)[CH:6]=[N:5]1.[O:42]=[CH:43][CH:44](CO)O.C([BH3-])#N.[Na+]>CO>[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]([C:16]3[C:35]([N:36]4[CH2:37][CH2:38][N:39]([CH2:44][CH2:43][OH:42])[CH2:40][CH2:41]4)=[CH:34][C:19]4[NH:20][C:21]([NH:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[C:30]([F:31])([F:32])[F:33])=[N:22][C:18]=4[CH:17]=3)=[O:15])[CH:11]=2)[CH:6]=[N:5]1

Komponenten

5

Edukt 3

HCID 751GlyceraldehydeHCID 5003444Sodium cyanoborohydrideHCID 178478620HCID 178478620, Verbindung

Produkt 1

HCID 178521766HCID 178521766, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 6-piperazin-1-yl-2-(2-trifluoromethylphenylamino)-1H-benzimidazole-5-carboxylic acid (1H-indazol-6-yl)-amide trihydrochloride (0.2 mmol; see Example 88) in methanol (2 mL) was added glyceraldehyde (2 mmol), and the resulting mixture was stirred at RT for 60 min. The reaction mixture was then charged with solid sodium cyanoborohydride (1 mmol), and the stirring was continued at RT for 10h. The reaction mixture was then concentrated in vacuo, and the residue was suspended in water (10 mL) with vigorous stirring. After 30 min, the solid was filtered, washed with water, and dried under vacuum to afford 6-[4-(2-hydroxyethyl)-piperazin-1-yl]-2-(2-trifluoromethyl-phenylamino)-1H-benzimidazole-5-carboxylic acid (1H-indazol-6-yl)amide as a white solid. MS: m/z 565 (M+H)+.

Aufarbeitung

  1. waitthe stirring was continued at RT for 10h
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. waitAfter 30 min
  4. filtrationthe solid was filtered
  5. washwashed with water
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-bc02f4da6c374bb89d661ef97cca3c1e
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820821B2

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