Water → tert-butyl methyl(2-(methyl((3-(3-(3-methylbut-2-enamido)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl)carbamate

HRID 570786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570786
C([C:3]1[C:4]([C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:26])[CH:22]=[C:23]([CH3:25])[CH3:24])[CH:17]=[CH:18][CH:19]=2)=[N:5][N:6]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)[CH:7]=1)=O.[CH3:27][N:28]([CH2:36][CH2:37][NH:38][CH3:39])[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32].[BH3-][C:41]#N.[Na+].O>CO.[Cl-].[Cl-].[Zn+2]>[CH3:27][N:28]([CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][C:3]1[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21](=[O:26])[CH:22]=[C:23]([CH3:25])[CH3:24])[CH:15]=2)=[N:5][N:6]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)[CH:7]=1)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32]

Komponenten

7

Edukt 4

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 14403871tert-Butyl methyl(2-(methylamino)ethyl)carbamateHCID 90425471N-(3-(4-formyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-yl)phenyl)-3-methylbut-2-enamide

Produkt 1

HCID 117617465tert-butyl methyl(2-(methyl((3-(3-(3-methylbut-2-enamido)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl)carbamateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of N-(3-(4-formyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-yl)phenyl)-3-methylbut-2-enamide (0.210 g, 0.00062 mol) in methanol (4 mL) were added TEA (313 mg, 0.0031 mol), ZnCl2 (0.008 g, 0.000062 mol) and tert-butyl methyl(2(methylamino)ethyl)carbamate (0.138 g, 0.00074 mol). The reaction mixture was stirred at rt for 45 min. NaCNBH3 (0.580 g, 0.00913 mol) was added and stirred for 2 h at rt. The reaction was poured into water (100 mL) and extracted with EtOAc (100 mL×2). The combined extracts was washed with brine (200 mL), dried over sodium sulphate and concentrated under vacuum. The residue was purified by SGC using DCM:MeOH (0%-4%) as eluent to obtain tert-butyl methyl(2-(methyl((3-(3-(3-methylbut-2-enamido)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl)carbamate (0.150 g, Yield: 47%). LCMS (ESI): RT=2.03 min, m/z=526.5 [M+H]+.

Aufarbeitung

  1. stirringstirred for 2 h at rt
  2. extractionextracted with EtOAc (100 mL×2)
  3. washThe combined extracts was washed with brine (200 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by SGC

Quellen und Nachweise

ORD-Eintrag
ord-73ffed1a8b99435f81da6e49dbe98276
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023883B2

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