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Sodium Hydroxide → (+/-) N-(3-{[2-(10-Aza-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-trien-4-ylamino)-5-trifluoromethyl-pyrimidin-4-ylamino]-methyl}-pyridin-2-yl)-methanesulfonamide

HRID 1161647
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Reaktionsgleichung

Reaktionsgleichung von HRID 1161647
C[N:2]([C:7]1[C:12]([CH2:13][NH:14][C:15]2[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][N:18]=[C:17]([NH:25][C:26]3[CH:36]=[CH:35][C:34]4[CH:33]5[CH2:37][CH:29]([CH2:30][N:31](C(=O)C(F)(F)F)[CH2:32]5)[C:28]=4[CH:27]=3)[N:16]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)[S:3]([CH3:6])(=[O:5])=[O:4].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCCC1>[CH:29]12[CH2:37][CH:33]([CH2:32][NH:31][CH2:30]1)[C:34]1[CH:35]=[CH:36][C:26]([NH:25][C:17]3[N:16]=[C:15]([NH:14][CH2:13][C:12]4[C:7]([NH:2][S:3]([CH3:6])(=[O:4])=[O:5])=[N:8][CH:9]=[CH:10][CH:11]=4)[C:20]([C:21]([F:22])([F:23])[F:24])=[CH:19][N:18]=3)=[CH:27][C:28]2=1
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Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 86623360(+/-) N-Methyl-N-(3-{[2-(10-trifluoroacetyl-10-aza-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-trien-4-ylamino)-5-trifluoromethyl-pyrimidin-4-ylamino]-methyl}-pyridin-2-yl)-methanesulfonamide

Produkt 1

HCID 68693452(+/-) N-(3-{[2-(10-Aza-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-trien-4-ylamino)-5-trifluoromethyl-pyrimidin-4-ylamino]-methyl}-pyridin-2-yl)-methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133
Benzyl triethylammonium chloride
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution 3 and tetrahydrofuran (2.00 mL) was treated with three crystals of benzyl triethyl ammonium chloride and 40% aqueous NaOH (2.00 mL), and the resultant bi-phasic reaction was heated to 70° C. under nitrogen. After sixteen hours, the mixture was allowed to cool to 25° C. The organic phase was collected and the aqueous layer was washed with EtOAc. The combined organic phases were dried over MgSO4, concentrated under reduced pressure, and purified over silica (92:8:0.8 CHCl3:CH3OH: NH4OH) to provide 32 g of 4 as a yellow foam). The yellow foam was dissolved in a minimum amount of CH2Cl2 at ° C., and 15 μL (0.0600 mmol) of 4.0 M HCl in 1,4-dioxane was slowly added. The resultant white slurry was stirred under a gentle flow of nitrogen for one hour and filtered to provide the hydrochloride salt from of 4 as a white solid (25 mg, 0.0474 mmol, 38%). C24H26F3N7O2S HPLC r.t.=5.10 min.; LC/MS (Method F) m/z 534.4 (MH+).

Aufarbeitung

  1. customthe resultant bi-phasic reaction
  2. waitAfter sixteen hours
  3. temperatureto cool to 25° C
  4. customThe organic phase was collected
  5. washthe aqueous layer was washed with EtOAc
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. custompurified over silica (92:8:0.8 CHCl3:CH3OH: NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-7ea7e166242545539ce93d4059e44f3a
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07820648B2

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