Diisopropylethylamine → 4-{4-[4-(3,4-Difluoro-phenyl)-1-(2-dimethylamino-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-ethyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one

HRID 1685210

Reaktionsgleichung

Reaktionsgleichung von HRID 1685210
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:12]([CH:14](N(C)C)[CH3:15])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[F:8].Cl[C:26]1[C:27]2[CH:34]([CH2:35][CH3:36])[C:33](=[O:37])[NH:32][C:28]=2[N:29]=[CH:30][N:31]=1.C[CH2:39][N:40](C(C)C)[CH:41](C)C>CC(O)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([CH:19]3[CH2:20][CH2:21][N:22]([C:26]4[C:27]5[CH:34]([CH2:35][CH3:36])[C:33](=[O:37])[NH:32][C:28]=5[N:29]=[CH:30][N:31]=4)[CH2:23][CH2:24]3)[N:12]([CH2:14][CH2:15][N:40]([CH3:41])[CH3:39])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 593223624-Chloro-5-ethyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-oneHCID 672647074-(3,4-difluorophenyl)-2-(piperidin-4-yl)-1H-imidazol-1-yl-N,N-dimethyl ethanamine

Produkt 1

HCID 593224564-{4-[4-(3,4-Difluoro-phenyl)-1-(2-dimethylamino-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-ethyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-oneAusbeute 26,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

Combine 2-(4-(3,4-difluorophenyl)-2-(piperidin-4-yl)-1H-imidazol-1-yl-N,N-dimethyl ethanamine (0.35 g; 0.0010 mol; 1.0 equiv), 4-chloro-5-ethyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (0.23 g; 0.0011 mol; 1.1 equiv), DIPEA (0.72 mL; 0.0041 mol; 4.0 equiv) in IPA (10 mL) and stir at 90° C. for 16 h. Quench the reaction with demineralized water and extract with EA. Evaporate the organic layer, purify over a silica gel column with 0-10% MeOH/DCM to give the title compound (0.13 g; 24.13%). MS (ES+): m/z=496 (M+H).

Aufarbeitung

  1. customQuench
  2. customthe reaction with demineralized water
  3. extractionextract with EA
  4. customEvaporate the organic layer
  5. custompurify over a silica gel column with 0-10% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-73108e1d496545288e9c16f1acb5350b
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148387B2

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