Triethylamine → 4-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid cyclopentylmethyl ester

HRID 1864107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1864107
N1([C:6](N2C=CN=C2)=[O:7])C=CN=C1.[CH:13]1([CH2:18][OH:19])[CH2:17][CH2:16][CH2:15][CH2:14]1.[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>[CH:13]1([CH2:18][O:19][C:6]([N:43]2[CH2:44][CH2:45][CH:40]([O:39][C:38]3[N:37]=[CH:36][N:35]=[C:34]4[N:30]([C:27]5[CH:28]=[CH:29][C:24]([S:21]([CH3:20])(=[O:22])=[O:23])=[CH:25][CH:26]=5)[N:31]=[CH:32][C:33]=34)[CH2:41][CH2:42]2)=[O:7])[CH2:17][CH2:16][CH2:15][CH2:14]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 77195CyclopentanemethanolHCID 113608021-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

Produkt 1

HCID 218978094-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid cyclopentylmethyl esterAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Di-imidazol-1-yl-methanone (0.51 mmol, 83 mg), and cyclopentyl-methanol (0.51 mmol, 51 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 A120 as a white solid (30 mg, 29%). Exact mass calculated for C24H29N5O5S 499.58, found 500.4 (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-bfc542202c7e416393b665c1382a8704
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625906B2

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