2-Ethyl-1-butanol → 4-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid 2-ethyl-butyl ester

HRID 1958377

Reaktionsgleichung

Reaktionsgleichung von HRID 1958377
N1([C:6](N2C=CN=C2)=[O:7])C=CN=C1.[CH2:13]([CH:15]([CH2:18][CH3:19])[CH2:16][OH:17])[CH3:14].[CH3:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:34]3=[N:35][CH:36]=[N:37][C:38]([O:39][CH:40]4[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]4)=[C:33]3[CH:32]=[N:31]2)=[CH:26][CH:25]=1)(=[O:23])=[O:22].C(N(CC)CC)C>CS(C)=O>[CH2:13]([CH:15]([CH2:18][CH3:19])[CH2:16][O:17][C:6]([N:43]1[CH2:44][CH2:45][CH:40]([O:39][C:38]2[N:37]=[CH:36][N:35]=[C:34]3[N:30]([C:27]4[CH:28]=[CH:29][C:24]([S:21]([CH3:20])(=[O:22])=[O:23])=[CH:25][CH:26]=4)[N:31]=[CH:32][C:33]=23)[CH2:41][CH2:42]1)=[O:7])[CH3:14]

Komponenten

6

Edukt 4

HCID 73582-Ethyl-1-butanolHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 113608021-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

Produkt 1

HCID 218977034-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid 2-ethyl-butyl esterAusbeute 44,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Di-imidazol-1-yl-methanone (0.51 mmol, 83 mg), and 2-ethyl-butan-1-ol (0.51 mmol, 52 mg) were dissolved in DMSO (1 mL) and stirred for 30 minutes at room temperature. Then, 1-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine (0.17 mmol, 70 mg) and triethylamine (0.51 mmol, 72 μL) were added and heated in a microwave at 120° C. for 6 minutes. The progress of the reaction was monitored by LCMS. The reaction mixture was quenched with water and the product was extracted with ethylacetate. Removal of organic solvents in vacuo and purification by HPLC provided Compound A119 as a white solid (38 mg, 36%). Exact mass calculated for C24H31N5O5S 501.60, found 502.3 (MH+).

Aufarbeitung

  1. temperatureheated in a microwave at 120° C. for 6 minutes
  2. customThe reaction mixture was quenched with water
  3. extractionthe product was extracted with ethylacetate
  4. customRemoval of organic solvents
  5. customin vacuo and purification by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-87049137b82b48588d3395c2fd9dcb60
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410119B2

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