Sodium Iodide → 1040718-40-8

HRID 1695204

Reaktionsgleichung

Reaktionsgleichung von HRID 1695204
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][N:12]=[C:11]([NH2:14])[CH:10]=2)=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.Br[CH2:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30].[I-].[Na+].[C:34]([N:37]1[CH2:43][CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)(=[O:36])[CH3:35]>CN(C)C=O>[C:34]([N:37]1[CH2:43][CH2:42][CH2:41][N:40]([CH2:25][CH2:26][CH2:27][CH2:28][C:29]([NH:14][C:11]2[CH:10]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[NH:13][N:12]=2)=[O:30])[CH2:39][CH2:38]1)(=[O:36])[CH3:35]

Komponenten

7

Edukt 5

HCID 5238Sodium IodideHCID 81531Diisopropylethylamine2×HCID 5211735-Bromovaleryl chlorideHCID 27564693-Amino-5-(4-methoxyphenyl)pyrazoleHCID 4186202N-Acetylhomopiperazine

Produkt 1

HCID 248605821040718-40-8Ausbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

To a solution of 5-(4-methoxyphenyl)-1H-pyrazol-3-ylamine (12 g, 62.8 mmol) and N,N-diisopropylethylamine (10.96 mL, 62.8 mmol) in dry N,N-dimethylformamide (150 mL) at −10° C. was added a solution of 5-bromovaleryl chloride (8.4 mL, 62.8 mmol) in dry N,N-dimethylformamide (50 mL) slowly (˜40 min) and the reaction mixture was allowed to stir at −10 to 0° C. for 8 hrs. Sodium iodide (9.44 g, 62.8 mmol) was added at 0° C. and followed by N-acetylhomopiperazine (8.24 mL, 62.8 mmol) and N,N-diisopropylethylamine (10.96 mL, 62.8 mmol) and the reaction mixture was allowed to stir at 50° C. for 18 hrs. The solvent was removed in vacuo. The residue was dissolved in methylene chloride (500 mL) and saturated aqueous sodium bicarbonate (500 mL) and the mixture was stirred at room temperature for 30 minutes. The organic layer was separated, dried over sodium sulfate, and the solvent was removed in vacuo to provide 25.8 g (99%) of 5-(4-acetyl-1,4-diazepan-1-yl)-N-(5-(4-methoxyphenyl)-1H-pyrazol-3-yl)pentanamide as a thick light yellow oil (crude).

Aufarbeitung

  1. stirringto stir at 50° C. for 18 hrs
  2. customThe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in methylene chloride (500 mL)
  4. stirringsaturated aqueous sodium bicarbonate (500 mL) and the mixture was stirred at room temperature for 30 minutes
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4c097c81e0d94457b203229c0c442b8b
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163729B2

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