Diisopropylethylamine → (3R)-1-{3-[1-(4-ethylphenyl)-1H-imidazol-5-yl]-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-N,N-dimethylpyrrolidin-3-amine

HRID 72720

Reaktionsgleichung

Reaktionsgleichung von HRID 72720
[CH3:1][N:2]([CH3:8])[C@@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)C(C)C)(C)C.Cl[C:19]1[N:24]=[CH:23][N:22]=[C:21]2[N:25]([CH3:41])[N:26]=[C:27]([C:28]3[N:32]([C:33]4[CH:38]=[CH:37][C:36]([CH2:39][CH3:40])=[CH:35][CH:34]=4)[CH:31]=[N:30][CH:29]=3)[C:20]=12>C(#N)C>[CH2:39]([C:36]1[CH:37]=[CH:38][C:33]([N:32]2[C:28]([C:27]3[C:20]4[C:21](=[N:22][CH:23]=[N:24][C:19]=4[N:5]4[CH2:6][CH2:7][C@@H:3]([N:2]([CH3:8])[CH3:1])[CH2:4]4)[N:25]([CH3:41])[N:26]=3)=[CH:29][N:30]=[CH:31]2)=[CH:34][CH:35]=1)[CH3:40]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 867125684-chloro-3-[1-(4-ethylphenyl)-1H-imidazol-5-yl]-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

Produkt 1

HCID 71114548(3R)-1-{3-[1-(4-ethylphenyl)-1H-imidazol-5-yl]-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-N,N-dimethylpyrrolidin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(3R)—N,N-Dimethylpyrrolidin-3-amine (12.4 mg, 0.109 mmol) and N,N-diisopropylethylamine (14.5 mg, 0.109 mmol) were added to a solution of 4-chloro-3-[1-(4-ethylphenyl)-1H-imidazol-5-yl]-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (C22) (37 mg, 0.11 mmol) in acetonitrile (1 mL), and the reaction mixture was stirred at room temperature for 2 hours. After removal of volatiles in vacuo, the residue was chromatographed on silica gel (Gradient: 0% to 15% ethyl acetate in methanol) to afford the product as a glass. Yield: 13 mg, 0.031 mmol, 28%. LCMS m/z 417.1 (M+1). 1H NMR (500 MHz, CDCl3), characteristic peaks: δ 1.17 (t, J=7.6 Hz, 3H), 2.49-2.65 (m, 8H), 3.51-3.61 (br m, 1H), 3.72-3.81 (br m, 1H), 4.08 (s, 3H), 7.10 (br d, J=8.3 Hz, 2H), 7.22-7.29 (m, 2H, assumed; partially obscured by solvent peak), 7.40 (br s, 1H), 7.90 (br s, 1H), 8.29 (s, 1H).

Aufarbeitung

  1. customAfter removal of volatiles in vacuo
  2. customthe residue was chromatographed on silica gel (Gradient: 0% to 15% ethyl acetate in methanol)

Quellen und Nachweise

ORD-Eintrag
ord-06dc7a16fb854803a3165109f5b159f5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829010B2

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