Diisopropylethylamine → 2-(5,5-Dioxo-5,10-dihydrophenothiazin-2-yl)-n-(1-methyl-1h-pyrazol-3-yl)-3-(tetrahydropyran-4-yl)propionamide

HRID 14997

Reaktionsgleichung

Reaktionsgleichung von HRID 14997
[O:1]=[S:2]1(=[O:27])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]2[CH:7]=[C:6]([CH:16]([CH2:20][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:17]([OH:19])=O)[CH:5]=[CH:4][C:3]1=2.[CH3:28][N:29]1[CH:33]=[CH:32][C:31]([NH2:34])=[N:30]1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1>CN(C)C=O.C(OCC)(=O)C>[O:1]=[S:2]1(=[O:27])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]2[CH:7]=[C:6]([CH:16]([CH2:20][CH:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[C:17]([NH:34][C:31]3[CH:32]=[CH:33][N:29]([CH3:28])[N:30]=3)=[O:19])[CH:5]=[CH:4][C:3]1=2

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 1372541-Methyl-3-aminopyrazoleHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 580242292-(5,5-Dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionic acid

Produkt 1

HCID 580242602-(5,5-Dioxo-5,10-dihydrophenothiazin-2-yl)-n-(1-methyl-1h-pyrazol-3-yl)-3-(tetrahydropyran-4-yl)propionamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

600 mg of 2-(5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionic acid, 120 mg of commercially available 1-methyl-1H-pyrazole-3-amine and 729 μl of N,N-diisopropylethylamine are dissolved in 5 ml of dimethylformamide. 561 mg of HATU and 200 mg of HOAT are added, and the mixture is stirred at room temperature for two hours. The reaction mixture is then diluted by addition of 200 ml of ethyl acetate and washed three times with in each case 50 ml of water and saturated sodium chloride solution. The organic phase is dried over MgSO4, and the solvent is then removed under reduced pressure. The residue is purified by RP-HPLC. This gives 200 mg of 2-(5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-N-(11-methyl-1H-pyrazol-3-yl)-3-(tetrahydropyran-4-yl)propionamide as a colorless lyophilisate.

Aufarbeitung

  1. washwashed three times with in each case 50 ml of water and saturated sodium chloride solution
  2. dry with materialThe organic phase is dried over MgSO4
  3. customthe solvent is then removed under reduced pressure
  4. customThe residue is purified by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-6d934af18b0a4f2baa267241da828b8e
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732440B2

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