Ammonium formate → 3-[(1-Methylethyl)oxy]-5-[(4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 548695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 548695
Cl[C:2]1[C:12]2[O:11][CH2:10][CH2:9][N:8]([CH3:13])[C:7](=[O:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][C:16]1[CH:17]=[C:18]([CH:28]=[C:29]([O:31][CH:32]([CH3:34])[CH3:33])[CH:30]=1)[C:19]([NH:21][C:22]1[CH:26]=[CH:25][N:24]([CH3:27])[N:23]=1)=[O:20].C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:34][CH:32]([O:31][C:29]1[CH:28]=[C:18]([CH:17]=[C:16]([O:15][C:3]2[CH:4]=[CH:5][C:6]3[C:7](=[O:14])[N:8]([CH3:13])[CH2:9][CH2:10][O:11][C:12]=3[CH:2]=2)[CH:30]=1)[C:19]([NH:21][C:22]1[CH:26]=[CH:25][N:24]([CH3:27])[N:23]=1)=[O:20])[CH3:33]

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 159494943-[(9-Chloro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-5-[(1-methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Produkt 1

HCID 159494953-[(1-Methylethyl)oxy]-5-[(4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of 3-[(9-chloro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-5-[(1-methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (160 mg, 0.32 mmol) in ethanol (3 mL) was added ammonium formate (208 mg, 10 equivs) in one portion. The reaction was blanketed with argon and 10% Palladium on carbon (40 mg) was added. The mixture was heated to 140° C. for 10 minutes in a Smith Creator microwave. The reaction mixture was filtered through diatomaceous earth and the filter pad was washed well with ethyl acetate. The filtrate was concentrated in vacuo and the residue purified by chromatography on alumina, eluting with 50-100% ethyl acetate in hexanes, to afford the title compound as a colourless oil which foamed under high vacuum (65 mg).

Aufarbeitung

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through diatomaceous earth
  3. washthe filter pad was washed well with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue purified by chromatography on alumina
  6. washeluting with 50-100% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e3f4949dbd674ccca4ddcab4335ff2d2
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943607B2

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