Glycine Hydrochloride → N-(2-Amino-2-oxoethyl)-3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)benzamide

HRID 549527

Reaktionsgleichung

Reaktionsgleichung von HRID 549527
C(N(CC)C(C)C)(C)C.[F:10][C:11]1[CH:12]=[CH:13][C:14]([O:48][CH3:49])=[C:15]([C:17]([CH3:47])([CH3:46])[CH2:18][C:19]([OH:45])([C:41]([F:44])([F:43])[F:42])[CH2:20][NH:21][C:22]2[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]3[C:23]=2[CH:24]=[N:25][N:26]3[C:32]2[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=2)[C:35](O)=[O:36])[CH:16]=1.CN(C(O[N:58]1N=[N:65][C:60]2C=CC=N[C:59]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.NCC(O)=[O:78]>CN(C=O)C>[NH2:58][C:59](=[O:78])[CH2:60][NH:65][C:35](=[O:36])[C:34]1[CH:38]=[CH:39][CH:40]=[C:32]([N:26]2[C:27]3[C:23](=[C:22]([NH:21][CH2:20][C:19]([OH:45])([C:41]([F:44])([F:43])[F:42])[CH2:18][C:17]([C:15]4[CH:16]=[C:11]([F:10])[CH:12]=[CH:13][C:14]=4[O:48][CH3:49])([CH3:46])[CH3:47])[CH:30]=[C:29]([CH3:31])[CH:28]=3)[CH:24]=[N:25]2)[CH:33]=1

Komponenten

6

Edukt 4

HCID 22316Glycine HydrochlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 251807833-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)benzoic acid

Produkt 1

HCID 24785985N-(2-Amino-2-oxoethyl)-3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)benzamideAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N,N-Diisopropylethylamine (0.109 mL, 0.625 mmol) was added to a solution of 3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)benzoic acid (70 mg, 0.125 mmol) and HATU (47.5 mg, 0.125 mmol) in DMF (2.5 mL) and the solution stirred at room temperature for 5 min. Glycine hydrochloride (34.6 mg, 0.313 mmol) was added and the mixture stirred at room temperature overnight and then partitioned between 2M HCl (50 mL) and ethyl acetate (50 mL). The organic layer was separated, washed with aqueous sodium bicarbonate (50 ml), dried over anhydrous sodium sulphate and evaporated to give crude product which was purified by mass directed autopreparation (System B) to give the title compound (62.5 mg).

Aufarbeitung

  1. stirringthe mixture stirred at room temperature overnight
  2. custompartitioned between 2M HCl (50 mL) and ethyl acetate (50 mL)
  3. customThe organic layer was separated
  4. washwashed with aqueous sodium bicarbonate (50 ml)
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated
  7. customto give crude product which
  8. customwas purified by mass

Quellen und Nachweise

ORD-Eintrag
ord-8a437f9e89b7498d88cfc092fddf4c17
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943651B2

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