Hydrochloric Acid → HCID 57594555, Verbindung

HRID 1436172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1436172
[OH:1][CH2:2][CH2:3][C@@H:4]([NH:24][C:25](=[O:31])OC(C)(C)C)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[C:19]([CH:20]([OH:22])[CH3:21])=[CH:18][CH:17]=[CH:16][N:15]3[CH:23]=2)=[CH:8][CH:7]=1.Cl.O1CCOCC1.C(N(CC)C(C)C)(C)C.[Cl:48][C:49]1[CH:50]=[C:51]([CH:66]=[CH:67][C:68]=1[O:69][CH:70]([CH3:72])[CH3:71])C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O>O>[Cl:48][C:49]1[CH:50]=[C:51]([CH:66]=[CH:67][C:68]=1[O:69][CH:70]([CH3:72])[CH3:71])[C:25]([NH:24][C@@H:4]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:13]=[C:14]3[C:19]([CH:20]([OH:22])[CH3:21])=[CH:18][CH:17]=[CH:16][N:15]3[CH:23]=2)=[CH:10][CH:11]=1)[CH2:3][CH2:2][OH:1])=[O:31]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 57594128HCID 57594128, VerbindungHCID 57594302HCID 57594302, Verbindung

Produkt 1

HCID 57594555HCID 57594555, VerbindungAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1,1-dimethylethyl [(1S)-3-hydroxy-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)propyl]carbamate (1.08 g, 2.54 mmol) and 4M HCl in 1,4-dioxane (8.0 mL, 32 mmol) was stirred at room temperature for 30 minutes. The reaction was concentrated to dryness redissolved in DMF (25 mL), and to this solution was added N,N-diisopropylethylamine (1.64 g, 12.7 mmol) and pentafluorophenyl 3-chloro-4 [(1-methylethyl)oxy]benzoate (0.963 g, 2.54 mmol). The mixture was stirred for 3.0 h at room temperature, diluted with water, and extracted into ethyl acetate. The extracts were washed with water and saturated sodium chloride, dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (2% MeOH:EtOAc) to give the title compound (0.7 g, 53%) as a pale yellow powder.

Aufarbeitung

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutionredissolved in DMF (25 mL)
  3. stirringThe mixture was stirred for 3.0 h at room temperature
  4. extractionextracted into ethyl acetate
  5. washThe extracts were washed with water and saturated sodium chloride
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (2% MeOH:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-c374ef4ef4ce4e37ab36d1da3fddf3b8
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618981B2

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