Glyoxylic Acid → HCID 178525831, Verbindung

HRID 388975

Reaktionsgleichung

Reaktionsgleichung von HRID 388975
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.[C:42]([OH:46])(=[O:45])[CH:43]=O.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[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]([CH2:43][C:42]([OH:46])=[O:45])[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

6

Edukt 3

HCID 760Glyoxylic AcidHCID 5003444Sodium cyanoborohydrideHCID 178478620HCID 178478620, Verbindung

Produkt 1

HCID 178525831HCID 178525831, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 6-piperazin-1-yl-2-(2-trifluoromethylphenylamino)-1H-benzimidazole-5-carboxylic acid (1H-indazol-6-yl)-amide trihydrochloride (0.25 mmol; see Example 88) in methanol (1 mL) was added glyoxylic acid (0.5 mmol), and the resulting mixture was stirred at RT for 60 min. The reaction mixture was then charged with solid sodium cyanoborohydride (0.6 mmol), and the stirring was continued at RT for 10 h. To the reaction mixture was then added a few drops of glacial acetic acid, and the mixture was stirred for 30 min. The volatiles were then removed 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 {4-[6-(1H-indazol-6-ylcarbamoyl)-2-(2-trifluoromethyl-phenylamino)-3H-benzoimidazol-5-yl]-piperazin-1-yl}acetic acid as a white solid. MS: m/z 579 (M+H)+.

Aufarbeitung

  1. waitthe stirring was continued at RT for 10 h
  2. stirringthe mixture was stirred for 30 min
  3. customThe volatiles were then removed in vacuo
  4. waitAfter 30 min
  5. filtrationthe solid was filtered
  6. washwashed with water
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6747d1cf0ba744fba1dbd0769009611e
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377983B2

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